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CollegeHumor

CollegeHumor is an comedy media company founded in December 1999 by college freshmen and as a featuring humorous content targeted at students, including memes, articles, and photos. Initially part of Connected Ventures, the site quickly gained popularity in the early era, expanding by into video sketches, merchandise via BustedTees, and other properties like Dorkly for gaming humor. In 2006, InterActiveCorp (IAC) acquired a majority stake in Connected Ventures for $26 million, providing resources that fueled CollegeHumor's growth into professional and television, including the MTV series The CollegeHumor Show (2009) and truTV's (2015–2019), while launching careers for talents like , , and . The company also ventured into film with (2013) and introduced the ad-free streaming service Dropout in 2018, focusing on unscripted comedy formats. By 2020, amid declining ad revenue from shifts to platforms and algorithm changes, IAC withdrew funding, leading to mass layoffs that reduced the staff from over 100 to about six employees. IAC's chief strategy officer then acquired the company for $0 (plus a minority stake retained by IAC), becoming CEO and pivoting to a subscription model emphasizing low-cost, long-form improv content like and the Dungeons & Dragons series . In September 2023, the brand fully rebranded as Dropout, dropping the CollegeHumor name across all platforms; in 2023, it achieved profitability with subscribers reaching the mid-to-high six figures (as of late 2023), generating 85% of revenue from $5.99 monthly fees, and expanded into live events, including a sold-out show at in January 2025.

History

Founding and Early Years (1999–2006)

CollegeHumor was founded in December 1999 by and , who were freshmen at the and the University of Maryland, respectively. The two childhood friends from , , launched the website as a platform for college-oriented humor, inspired by the ad revenue potential of similar sites like JoeCartoon.com, which reportedly earned $20,000 monthly. With an initial investment of about $150 each, they built the site using basic tools like and initially hosted it on a page before upgrading to a dedicated domain. The launch targeted undergraduates by aggregating and sharing lighthearted, relatable content from campus life. In 2000, the founders recruited programmer Jake Lodwick from the and designer from as partners to handle technical and creative demands. In its early years, CollegeHumor focused primarily on user-submitted material, including jokes, humorous essays, photoshopped images, and contests such as the "Election Erection ’04" photo manipulation challenge, which received over 300 entries. Visitors contributed daily updates like dorm-room photos, short videos, and articles on topics such as "Everything I Learned About Life I Learned in First Semester," fostering a community-driven forum for sophomoric humor. The site promoted itself through flyers distributed at universities and incentives like free t-shirts for submissions, leading to rapid growth; traffic increased 300% in the 18 months following the founders' graduation in 2003. By late 2004, it attracted nearly 8 million unique monthly visitors, with revenue reaching $405,000 in December alone, up from $45,400 the previous year, largely from low-overhead advertising and affiliate partnerships. Following graduation, Abramson and Van Veen briefly relocated operations to before moving the headquarters to a 5,000-square-foot in City's Tribeca neighborhood in the summer of 2004 to capitalize on the burgeoning scene. Additional staff, including writers and performers such as , who started as an intern, and , hired as a writer post-college, joined around 2006 to support expanding production. Key milestones included the October 2004 upload of the "SNL" lip-sync clip, which drew nearly 1 million views in two days, and the launch of in November 2004 for better video hosting, alongside early experiments with original sketches beginning in 2005. Funding remained bootstrapped through display ads via networks, merchandise like the patented Big Shocker foam hand (selling ~20,000 units), and the 2004 debut of BustedTees for custom apparel, establishing profitability without external investment until later.

IAC Ownership and Expansion (2006–2020)

In August 2006, InterActiveCorp (IAC) acquired a 51% controlling stake in Connected Ventures, the parent company of CollegeHumor, for an undisclosed amount estimated at around $20 million. This transaction integrated CollegeHumor into IAC's growing portfolio of properties, initially operating under the Connected Ventures umbrella before evolving into the CH Media division, which focused on and content. Under IAC's ownership, CollegeHumor shifted from toward professional , marking a significant scaling of operations. Following the acquisition, CollegeHumor expanded its video production capabilities starting in 2006, hiring key talent such as as director of original content to oversee the creation of in-house sketches and series. This period saw the production of thousands of original videos, with the company launching specialized sites like Dorkly in June 2010, dedicated to gaming humor through articles, animations, and videos, and Drawfee in March 2014, focusing on art-based comedy challenges and illustrations. These initiatives diversified CollegeHumor's offerings and attracted niche audiences, supported by IAC's resources for talent acquisition and content development. By the mid-2010s, CollegeHumor had launched mobile apps, including the 2013 photo game Bout, and pursued international reach through global distribution on platforms like , achieving peak monthly video views exceeding 100 million across its properties by around 2015. The company formed partnerships with for video hosting and monetization, as well as early streaming services like , to broaden its audience beyond the U.S. However, the late brought challenges amid a declining digital advertising market, leading to operational cutbacks. In , CollegeHumor launched Dropout as an ad-free subscription streaming service at $5.99 per month, aiming to diversify revenue through exclusive comedy content like unscripted series and animations. In 2019, the company shut down new content production on Dorkly and other verticals due to unsustainable ad revenues, followed by significant layoffs in 2020 as IAC prepared to divest. These moves reflected broader industry pressures on ad-dependent , with CollegeHumor producing over 5,000 sketches during its IAC era before transitioning toward subscription models.

Transition to Dropout and Recent Developments (2020–present)

In January 2020, IAC divested CH Media, the parent company of CollegeHumor, by transferring majority ownership to , its longtime and , at no monetary cost. IAC sold CH Media to at no monetary cost. This resulted in the of over 100 employees (out of about 105), leaving a core team of approximately 7 to continue operations focused on the Dropout streaming service. The acquisition marked a pivotal shift toward independence, enabling the company to pivot from ad-supported content to a subscription-based model without corporate oversight. By September 2023, the company fully rebranded from CollegeHumor to Dropout, retiring the longstanding CollegeHumor YouTube channel with over 14 million subscribers and redirecting efforts to the ad-free Dropout platform launched in 2018. This rebranding aligned the company's identity with its streaming service, emphasizing unscripted comedy and original series. Dropout's subscriber base, which reached around 350,000 by the end of 2022, grew significantly and nearly doubled to the mid-six figures by the end of 2023, driven by expanded content output and word-of-mouth promotion. The rebrand facilitated expansion into live events, capitalizing on fan engagement with series like Dimension 20. In 2024 and 2025, Dropout hosted multiple sold-out shows, culminating in a landmark performance at on January 24, 2025, which drew over 19,500 attendees for a live adaptation. This event highlighted the company's growing cultural impact in the comedy and gaming communities. Recent developments include the 2024 launch of Dropout Presents, a series of live-recorded comedy specials featuring stand-up and improv, with Season 2 premiering in November 2025 and spotlighting performers such as , Mark Vigeant, , and Michael Cruz Kayne. In 2025, platform enhancements improved user experience through a subscription adjustment to $6.99 monthly (effective May), the introduction of a Superfan tier offering and exclusive perks, and technical upgrades like streamlined navigation and URL redirects. Dropout's ad-free, subscription-only model has sustained robust growth, supported by significant growth, including over 50% increase in subscribers in 2023, and subscriber expansion to more than one million by late 2025.

Original Content

Website Sketches and Articles

CollegeHumor's original website content primarily consisted of text-based humorous articles, lists, and opinion pieces targeting college students and young adults, focusing on topics such as campus life, pop culture, and emerging internet trends from its launch in 1999 through 2018. These included comedic essays, joke compilations, and illustrated features like user-submitted images and offensive humor sections in CollegeHumor Raw, which hosted "too dirty" pictures and edgy written content. Examples encompassed list-style pieces, such as compilations of quotes from films like those in the Will Ferrell canon, alongside satirical takes on elections and celebrity culture. The platform emphasized interactive elements to foster , including submissions of photos and images, forums for discussion, and contests like the 2004 "Election Erection" challenge that encouraged humorous image manipulations. By , the site published daily original articles alongside a steady of user contributions, reaching a peak of over 200 million monthly page views and more than 6 million unique monthly users. This volume of non-video material, often featuring guest-like user inputs, helped establish CollegeHumor as a pioneer in early humor by aggregating and amplifying shareable, meme-like content. Over time, the site's text-based offerings evolved from a chaotic repository of user-submitted images and basic jokes to more structured illustrated humor and polished articles, incorporating while retaining community-driven elements. This foundation supported the development of in-house talent through written contributions, though the emphasis gradually shifted toward video sketches by the late 2000s. At its height, the website's non-video content influenced the broader landscape of online comedy by popularizing accessible, relatable formats that resonated with young audiences.

Web Series

CollegeHumor's web series represented a cornerstone of its original video content, featuring scripted, short-form comedies primarily produced in-house and distributed via the company's website and YouTube channel. These series emphasized relatable humor drawn from everyday scenarios, particularly office and college life, and were crafted with a focus on quick production cycles to capitalize on viral potential in the early era of online video. The output included hundreds of episodes across multiple flagship shows, contributing to the platform's reputation as a pioneer in digital sketch comedy. Many of these series' episodes are archived and available on Dropout's streaming platform and YouTube channel following the 2023 rebrand. One of the most enduring series was , an office-based comedy starring and as mismatched coworkers, which ran from 2007 to 2015 under the CollegeHumor banner. Spanning over 750 episodes, the show evolved from improvised shorts filmed after hours with basic equipment to more structured scripts supported by a dedicated crew, amassing more than half a billion views by the end of its run with CollegeHumor. Its low-key, character-driven format captured the awkward dynamics of workplace friendships, blending absurdity with subtle humor that resonated with audiences. Another prominent series, , debuted in 2007 and continued through 2019, depicting satirical vignettes of unprofessional antics among the fictionalized CollegeHumor staff in their . Comprising 16 seasons and 322 episodes (as per the official playlist), it exemplified the company's signature style of short-form sketches, typically 2 to 5 minutes in length, shot on modest budgets using spaces as sets to highlight themes of , , and corporate . The series maintained a raw, improvisational edge while poking fun at media industry tropes, becoming a staple for fans seeking bite-sized entertainment. CollegeHumor's often featured experimental parodies of collegiate experiences, such as early efforts mimicking campus life and student media, though these were shorter-lived compared to ongoing office comedies. Production across all series prioritized accessibility, with videos uploaded directly to and CollegeHumor.com, resulting in a catalog exceeding 2,000 original clips by the late that collectively drove billions of views on the channel. This approach not only built a massive online following but also served as a launchpad for emerging talent, including performers like , who joined in 2017 and gained prominence through sketch roles before transitioning to broader comedy projects. Notable extensions from these web efforts included precursor sketches that informed The CollegeHumor Show, a 2009 MTV series blending office with standalone bits, as well as occasional guest collaborations that infused episodes with external star power to boost visibility. Overall, the web series amassed over 7 billion views by 2022, underscoring their role in defining early internet humor and fostering a community around shareable, low-stakes .

Television Productions

CollegeHumor ventured into traditional television with The CollegeHumor Show, a scripted comedy series that premiered on on February 8, 2009. The show blended mockumentary-style glimpses into the daily lives of CollegeHumor's editorial staff with adapted sketches from their popular web content, featuring core cast members including , , , and as fictionalized versions of themselves navigating office antics and creative chaos. Spanning six half-hour episodes that aired weekly through March 15, 2009, the series marked CollegeHumor's first major broadcast adaptation, emphasizing higher-budget live-action production over their digital shorts while retaining the irreverent humor rooted in web origins. Reception was generally positive among fans for its authentic portrayal of the company's dynamic, earning an IMDb user rating of 7.7 out of 10, though it did not lead to renewal due to modest viewership in MTV's late-night slot. In 2015, CollegeHumor co-produced Adam Ruins Everything, an educational comedy series hosted by alumnus that debuted on and ran for three seasons until 2019. The show, which expanded on Conover's CollegeHumor web segments debunking common misconceptions, featured 65 episodes where Conover humorously dismantled myths about , , and society using expert interviews and animations. Produced in collaboration with and CollegeHumor's in-house team, it shifted toward polished, narrative-driven live-action formats with recurring CollegeHumor contributors like and Brian Murphy in supporting roles. Critically acclaimed for its witty —garnering an 8.1 rating—the series attracted a dedicated audience through its blend of entertainment and information, though specific episode viewership figures remained undisclosed by the network.

Books

CollegeHumor expanded its into with a series of humor , primarily compilations of satirical content adapted from its website articles and sketches, targeting young adults with absurd advice on everyday life, social interactions, and . These publications were written collectively by the site's staff writers and illustrated to enhance their comedic appeal. The company's debut book, The CollegeHumor Guide to College: Selling Kidneys for Beer Money, Sleeping with Your Professors, Majoring in Communications, and Other Really Good Ideas, was released in April 2006 by Dutton, a division of (now ). This 368-page hardcover humor guide offers exaggerated, tips on navigating life, including dorm , partying strategies, and academic shortcuts, all presented in the site's signature witty style. Written primarily by columnists Ethan Trex and , it draws from popular online content to provide a mock survival manual for freshmen. In 2008, CollegeHumor followed with Faking It: How to Seem Like a Better Person Without Actually Improving Yourself, published by , an imprint of Penguin. This 288-page extends the brand's satirical take on self-improvement, featuring humorous essays and lists on pretending to be cultured, fit, or intellectually superior through minimal effort, such as faking book knowledge or gym habits. Authored by the Writers of CollegeHumor.com, it satirizes pop psychology and lifestyle trends prevalent among young professionals and students. The brand's third major print outing, CollegeHumor: The Website. The Book., appeared in August 2011 from Da Capo Press, a imprint. This 288-page anthology compiles standout articles from the site's first decade, including pieces like "Drunk-O-Vision" and "The Riddler Gets Lazy," edited by . It serves as a of CollegeHumor's text-based humor, emphasizing absurd scenarios and pop parodies, and was marketed as a bridge between the digital and physical formats of the company's content. These books were distributed through major retailers like and independent bookstores, reflecting CollegeHumor's effort to monetize its online popularity in traditional channels during its IAC . They collectively highlight the company's focus on relatable, over-the-top for a millennial audience navigating post-college transitions.

Dropout Platform

Overview and Launch

Dropout is a subscription-based streaming service launched by CH Media, the parent company of CollegeHumor, on September 26, 2018. It debuted as an ad-free platform offering access to the CollegeHumor video archives, including over 1,500 titles, alongside new original programming, with a public priced at $3.99 per month before transitioning to a standard rate of $5.99 monthly or $49 annually. The service was positioned as a alternative to ad-supported platforms, emphasizing comedy content without interruptions. In September 2023, coinciding with its fifth anniversary, the company fully rebranded from CollegeHumor to Dropout, marking a complete pivot to the streaming platform as its core identity. This rebrand included updates to the and apps for improved , and by late 2023, Dropout had nearly doubled its subscriber base to the mid-six figures. As of November 2025, the service surpassed 1 million subscribers, reflecting sustained growth amid a challenging streaming landscape. By 2025, enhancements to the platform included the introduction of a "Superfan" tier at a higher for additional perks and expanded support for events, building on earlier announcements of live specials. Dropout's content strategy centers on unscripted formats such as improv comedy, game shows, and games (RPGs), which allow for efficient production and high audience engagement compared to scripted content. The platform operates without traditional advertisements, relying instead on subscription revenue and merchandise sales through its integrated store for funding. Technically, Dropout supports on-demand streaming across web and mobile devices, with offline download capabilities available via its and apps for select videos. It also integrates with by offering free clips and previews to drive traffic to the paid service, leveraging the channel's 15 million subscribers for promotion.

Game Shows

Dropout's game shows represent a core pillar of its programming, featuring , panel-based competitions that blend , , and absurdity to engage audiences with pop culture and humor. These formats emphasize competitive play among comedians and guests, often revolving around correcting inaccuracies or adapting to unexpected rules, fostering high-energy interactions without scripted dialogue. "Um, Actually," which premiered in 2018, is a trivia correction game hosted by Ify Nwadiwe with fact-checking by David Gilbert, where three contestants compete to identify and correct deliberate errors in statements about nerdy topics like sci-fi, comics, and music. Created by Mike Trapp, the show has produced over 100 episodes across 10 seasons, with gameplay structured around rounds of escalating questions that reward precise pedantry, such as naming obscure details from franchises like Star Wars or . Notable guests have included , , and Matt Mercer, adding layers of expertise and celebrity appeal to the panels. The format's unscripted nature highlights contestants' encyclopedic knowledge, often leading to humorous tangents and rivalries among recurring players from roster. "Game Changer," launched in 2019 and hosted by Dropout CEO , is a that introduces a entirely new premise and rule set for each episode, challenging contestants to deduce and adapt to the unknown objective while competing in themed challenges drawn from pop culture, wordplay, or physical comedy. Spanning seven seasons with more than 50 episodes, it features panels of improvisers and comedians, such as and Ally Beardsley, engaging in absurd scenarios like or invention-based games, with production elements like surprise twists enhancing the unpredictability. The show has generated spin-offs, including "Dirty Laundry," which evolved from a 2020 "" episode into a standalone series focused on confessional-style revelations. In 2024, "" was submitted for Emmy consideration in categories like Outstanding , recognizing its innovative format. Both shows have garnered strong reception for their clever premises and talented ensembles, with "Um, Actually" holding an 8.3/10 rating on IMDb from nearly 500 user reviews praising its niche appeal to fandom enthusiasts, and "Game Changer" earning a 9.2/10 from over 2,000 reviews for its consistent creativity and emotional depth in low-budget production. Critics have highlighted their high engagement, with outlets noting viewer retention through relatable humor and replay value, often exceeding 90% positive sentiment in aggregated feedback. These series exemplify Dropout's model of accessible, ad-free improv comedy that prioritizes performer chemistry over high-stakes prizes.

Role-Playing Series

Dimension 20 is Dropout's flagship actual-play (RPG) series, premiering in 2018 and featuring comedian as the primary game master (GM) or (DM). The anthology format presents self-contained campaigns, primarily using the 5th edition ruleset, with each season exploring unique worlds and narratives driven by ensemble casts of improvisational performers. As of 2025, the series encompasses 26 seasons and over 280 episodes, blending high-stakes storytelling, humor, and character-driven drama to engage audiences in collaborative experiences. The series' production involves live recordings in a dedicated studio with a multi-camera setup and immersive set design, such as a for spatial effects, followed by editing to enhance pacing and visual elements for streaming on Dropout. This approach allows for unscripted player decisions to shape the narrative while maintaining professional polish, distinguishing it from raw convention streams. operates under a licensing agreement with , the publishers of , enabling official use of their and contributing to broader TTRPG promotion. Casts emphasize in , , and , with recurring players like the "Intrepid Heroes" (Ally Beardsley, Brian Murphy, , Lou Wilson, , and Zac Oyama) alongside guests such as , who has both played roles like pirate captain Antiope Jones in Pirates of Leviathan and served as GM for campaigns including Burrow's End. Seminal seasons include Fantasy High (2018, 20 episodes), which follows a group of high school students uncovering threats in a suburban town, and The Unsleeping City (2019, 17 episodes), reimagining as a magical realm where everyday heroes battle existential forces. These campaigns exemplify Mulligan's style of weaving personal stakes with epic fantasy, fostering emotional depth through player improvisation. Follow-up arcs like Fantasy High: Junior Year (2023) and The Unsleeping City: Chapter II (2020) expand these universes, maintaining continuity for fans while introducing new challenges. Expansions have extended the series beyond streaming, with live tours commencing in 2023 and continuing through 2025, including sold-out performances like Time Quangle across the and in 2024, Gauntlet at the Garden at in January 2025, and upcoming shows such as Battle at the Bowl at the . These events adapt campaigns for theatrical audiences, often incorporating audience interaction and . Spin-offs like the heist-themed Tiny Heist (2021, 6 episodes), featuring miniature criminals in a noir world, and the swashbuckling Pirates of Leviathan (2022, 6 episodes), a live-recorded adventure on the high seas, showcase shorter formats that test experimental premises while retaining core ensemble chemistry. Dimension 20 has significantly expanded the mainstream appeal of RPGs, drawing in newcomers through its accessible humor and inclusive narratives, as evidenced by its role in the TTRPG resurgence alongside shows like . The series has garnered critical acclaim for advancing LGBTQ+ representation in gaming media, with seasons like Dungeons and Drag Queens earning the 2025 Award for its celebration of drag culture in fantasy settings. Its influence is further highlighted by adaptations, such as the Fantasy High launched on in March 2025, and cumulative viewership exceeding tens of millions across platforms, including over 7.9 million for the premiere episode of Fantasy High on alone.

Improv and Talk Shows

Dropout's improv and talk shows emphasize through ensemble performances and spontaneous interactions, distinguishing them from the platform's more . These formats draw on the improvisational roots of CollegeHumor's original content, adapting them for the streaming era with a focus on guest comedians reacting to unexpected scenarios. "Very Important People," which premiered on December 15, 2023, features host Vic Michaelis conducting fully improvised interviews with comedians transformed via makeovers into absurd characters. Guests, including Anna Garcia as Princess Emily and as Augbert, receive prompts that lead to satirical discussions on topics like advocacy or celebrity personas, blending tropes with surreal humor. The series spans two seasons with 24 episodes as of 2025, earning a Webby Award for its innovative structure. "Make Some Noise," hosted by Sam Reich since its November 9, 2020, debut, is a sound-based improv series where guest comedians, such as and the Noise Boys (, Zac Oyama, and ), act out prompts using only vocal effects and impressions. Prompts range from everyday scenes to fantastical scenarios, encouraging rapid ensemble collaboration without props or visuals. By 2025, the show has released four seasons totaling over 70 episodes, released biweekly, and has become a staple for its accessible entry into improv comedy. "Breaking News: No Laugh Newsroom," originating in 2018 but peaking in popularity from 2021 to 2023, simulates a news broadcast where reporters like Ify Nwadiwe and read from teleprompters filled with intentionally ridiculous stories, penalized for laughing. The format highlights improvisational restraint and reaction, with episodes featuring escalating absurdity such as reports on " water composition" or political parodies. It concluded after seven seasons and approximately 90 episodes, transitioning elements to live tours. (Note: Fandom is secondary, but corroborated by official episode counts.) These shows incorporate audience-submitted prompts in select episodes to fuel spontaneity, underscoring Dropout's commitment to ensemble-driven comedy that evolves with viewer input. In 2025, segments from "Very Important People" and "Make Some Noise" crossed over into the Dropout Improv Tour, adapting studio improv for live audiences across U.S. cities like and . This integration has amplified their impact, with tour dates selling out rapidly and fostering direct fan engagement.

Other Programming

Dropout's other programming encompasses a range of specials, archived materials, and innovative formats that expand beyond its flagship game shows, role-playing, and improv series, offering subscribers diverse comedic experiences. "Dropout Presents," which debuted in 2024, is a flagship series of live-recorded comedy specials featuring stand-up, improv, and solo performances captured before audiences. The inaugural season included notable entries such as Cameron Esposito's "Four Pills," premiering on April 11, 2025, where the comedian delves into their late diagnosis of bipolar disorder and the preceding life events. Season 2, announced in October 2025, introduces fresh specials from talents including Mark Vigeant's "The Best Man Show," slated for February 25, 2026, and Demi Adejuyigbe's "Is Going To Do 1 (One) Backflip," set to premiere on November 19, 2025. These specials highlight Dropout's commitment to showcasing established and rising comedians in intimate, unscripted environments. The platform also maintains an archive of curated CollegeHumor classics, including original sketches, the "Hardly Working" series, and various one-off videos from the company's pre-2018 era, comprising over 1,500 pieces of content that preserve the foundational humor of Dropout's predecessor. Among the distinctive one-offs is "Smartypants," a debate-style show hosted by Rekha Shankar, in which participants deliver passionate, absurd presentations on topics ranging from birthdays and to and conspiracy theories; the series launched in April 2024 and continued with a second season in March 2025. Emerging formats further diversify the lineup, such as "Gastronauts," a culinary improv competition that premiered on October 11, 2024, and pits professional chefs against bizarre, comedian-devised challenges under host Jordan Myrick's guidance. Renewed for a second season premiering August 15, 2025, it blends food experimentation with spontaneous comedy. Recordings from live events, including the Dropout Improv tours spanning 2024 and 2025 across U.S. cities like and , are selectively added to the platform, capturing high-energy performances. These elements often integrate with Dropout's merchandise offerings, such as themed apparel and accessories tied to , alongside fan-engaged features like voting mechanisms for episode twists or revival considerations, contributing to a niche library of over 500 hours of specialized content.

Personnel

Founders and Executives

CollegeHumor was founded in 1999 by Josh Abramson and Ricky Van Veen, two high school friends from Baltimore who launched the site as college freshmen to share humorous content targeted at young adults. Abramson and Van Veen provided the initial vision for the platform, starting with user-submitted jokes and sketches that quickly grew into a major online comedy destination, eventually attracting acquisition by InterActiveCorp (IAC) in 2006. Van Veen served as CEO during much of the site's early expansion, overseeing its transition from a simple humor repository to a multimedia production company before departing in 2016 to join Facebook as head of global creative strategy. Sam Reich joined CollegeHumor in 2006 as director of original content and rose through executive ranks, becoming president of original content by 2011 and by the late 2010s. As , played a pivotal role in launching the Dropout streaming service in September 2018, shifting the company toward ad-free, subscription-based original programming to compete in the evolving landscape. In January 2020, amid IAC's withdrawal of funding and massive layoffs, acquired the company for no upfront cost, retaining a to sustain operations and reposition it for independence. Under his leadership as CEO of Dropout since 2020, orchestrated a successful turnaround, culminating in the full rebranding of CollegeHumor to Dropout in September 2023 to emphasize the streaming platform's focus on and audience engagement. By 2025, this strategy had expanded to live events, including sold-out performances at and improv shows in cities like , marking a shift toward hybrid online-offline experiences. Other key executives post-2020 include , who has served as a core creative leader at Dropout, functioning as and for flagship series like while contributing as a and performer to maintain the platform's innovative comedy output during its leanest periods.

Notable Alumni and Contributors

CollegeHumor and its successor platform Dropout have launched the careers of numerous performers, writers, and creators who have achieved prominence in comedy television and film. Among the most notable are and , who rose to fame through their long-running Jake and Amir, produced by CollegeHumor from 2007 to 2015, which featured the duo portraying exaggerated versions of themselves in absurd office scenarios. The series amassed millions of views and led to spin-off projects, including the advice podcast If I Were You, which they continue to host independently. Early contributors and appeared as special guests in CollegeHumor's annual All-Nighter events, showcasing their comedic chemistry in sketches that foreshadowed their breakthrough work. Their involvement with the company helped build their profiles in the comedy scene, ultimately paving the way for the development of , the series they co-created and starred in from 2014 to 2019, which drew from their earlier web series and earned critical acclaim for its portrayal of young women in urban life. In the realm of role-playing game content on Dropout's Dimension 20, regulars Ally Beardsley and Lou Wilson have become fan favorites for their improvisational skills and character work across multiple seasons. Beardsley, known for roles like the chaotic Liam Wilhelmina in A Crown of Candy, has expanded into indie projects such as the DownBeat (2019) and the Genderspiral, while Wilson, who played the noble Ricky Matsui in The Unsleeping City, transitioned to dramatic roles in Netflix's (2017–2018) and Hulu's (2017–2019). Similarly, writers and performers and Brian Murphy (often credited as "Murph") have been integral to Dimension 20, with Axford portraying characters like the scheming Amethar Rocks in A Crown of Candy and Murphy as the heroic Ballaster Kodaka; the couple co-created the Pop TV series [Hot Date](/page/Hot Date) (2017–2018) and host the Not Another D&D Podcast. Guest stars like contributed to early CollegeHumor sketches, including the 2006 video "Cures for Hangovers," where he delivered deadpan humor on absurd remedies, marking one of his initial forays into on-camera comedy before his stand-up specials and writing for . The company's alumni have had significant career impacts, with many securing roles and writing positions on major television programs. For instance, writers like and have contributed to , with Schneider serving as an Emmy-nominated head writer and Seidell penning sketches for high-profile hosts; Dan Gurewitch earned an Emmy for his work on ; and writes for . Other notable transitions include starring in and producing for and Brian Murphy appearing in the series as well. In 2025, , a key creative force behind , expanded his influence by taking on the Dungeon Master role for Critical Role's Campaign 4, premiering in October, alongside directing live productions like at .

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