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Jay Pinkerton
Jay Pinkerton
Jay Pinkerton
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Jay Pinkerton (born June 15, 1977) is a Canadian humourist known for co-writing, with Erik Wolpaw, the story of Valve's video game Portal 2.[1] A former editor of both Cracked.com and Cracked magazine, PlayStation World magazine referred to him as a "one-man gag machine".[2] Prior to joining Cracked, Pinkerton served as the managing editor of NationalLampoon.com, the website of the national comedy and film brand.

Key Information

Jay Pinkerton initially registered his website, Jaypinkerton.com, to be a portfolio of his comedy and artwork. Afterwards, Pinkerton joined the forums of the Internet humour website "Pointless Waste of Time" (PWOT), and took the attention of the site's owner, David Wong, with whom Pinkerton worked on a now-defunct satirical news commentary, the "News Skim", and other comedy articles. Around this time, he first published his redone Spider-Man comics, spawning an internet phenomenon.

In addition to Cracked, Pinkerton's work has also appeared on McSweeney's Internet Tendency, Modern Humorist, CollegeHumor.com and numerous other sites. He has also had his humour writing published in print, including in Jest Magazine, McSweeney’s Best Non-Required Reading 2003, National Lampoon’s Big Book of Love, The CollegeHumor Guide to College and Golden Words.

Pinkerton joined Valve in 2008 and served as a writer for their games. In June 2017, he announced he had left Valve for unspecified reasons.[3] However, he returned to resume working as a writer for Valve in July 2018.[4] Some of his work on return included writing for Half-Life: Alyx, the first original AAA VR title released in 2020.[5] Pinkerton worked as a writer on Team Fortress comics and helped confirm the release of the seventh and final issue in 2024.[6]

References

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Jay Pinkerton

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Jay Pinkerton is a Canadian and renowned for his contributions to Valve Corporation's acclaimed titles, particularly co-writing the story for (2011) alongside and . Born and raised in , Pinkerton developed his comedic style early, drawing influences from works like and , and serving as editor of his university's humor publication, Golden Words. After studying English with a minor in classics, he pursued a career in comedy writing, becoming a managing editor at National Lampoon's website before joining as an editor and contributor, where he produced satirical articles and greeting card parodies that showcased his non-sequitur humor. In 2008, Pinkerton transitioned to video game writing at , where he co-authored scripts for (2008) and (2009), and expanded the universe through comics and animated shorts like Jungle Inferno. After departing the company in 2017 amid a wave of writer exits, he rejoined in 2018 and has continued working there as of 2025, including co-writing Half-Life: Alyx (2020) with Wolpaw and , addressing key narrative challenges such as the game's status and its timeline-altering ending involving the G-Man character. Pinkerton's work on Alyx has been credited with revitalizing interest in the series, with him expressing enthusiasm for potential future installments that explore new storylines stemming from the game's conclusion.

Early life and education

Early life

Jay Pinkerton was born in , Canada. As a Canadian, he spent his formative years in this modest college town, often referred to as Canada's prison capital due to its historical institutions. Pinkerton's family environment was intellectually oriented but not overtly comedic; his father, an English major and local teacher, fostered a reading-heavy household that introduced him to influential comic strips such as and from a young age. Despite financial constraints, his parents demonstrated creativity by handcrafting a Batman puzzle for him as a , sparking early engagement with popular culture. In high school, as a skinny and self-described awkward teen, Pinkerton began using humor as a defense mechanism against potential , marking his initial foray into making others laugh. His childhood hobbies centered on cartooning and satire, reflecting a budding creative development. Pinkerton aspired to become a comic strip writer and produced his own rudimentary series, including Hot and Ham, a detective parody inspired by Archie Comics and Inspector Gadget. These efforts, along with influences from satirical works like Bloom County and the sketch comedy troupe Kids in the Hall, honed his affinity for witty, observational humor during the late 20th century in Canada. This foundation in Kingston propelled Pinkerton toward formal education at Queen's University.

Education

Jay Pinkerton attended Queen's University in Kingston, Ontario, where he earned a Bachelor of Arts in English with a minor in classics. During his time at the university, Pinkerton immersed himself in the campus's vibrant creative scene, particularly through the student-run humor publication Golden Words. Starting as a cartoonist, he contributed satirical illustrations and writings that evolved into more structured comedy pieces over his four years, serving eventually as the paper's editor; this hands-on experience in satirical humor and editing sharpened his skills in concise, witty prose more effectively than formal coursework. As a , Pinkerton began developing his personal , jaypinkerton.com (later hosted under a subdomain), as a digital portfolio to showcase his early cartoons, humorous articles, scripts, and plays—such as "Why I Probably Shouldn't Do Stand-Up"—allowing him to experiment with and refine his satirical voice beyond the university's print outlets.

Career

Early career in humor writing

Jay Pinkerton began his professional career in humor writing in the early 2000s as a freelance cartoonist and writer, drawing inspiration from comic strips like and . While studying at Queen's University, he served as editor of the student-run humor publication Golden Words for four years, starting with cartoons before shifting focus to writing satirical pieces. This experience provided foundational skills in comedy, allowing him to transition into freelance contributions for various outlets. In the mid-2000s, Pinkerton contributed satirical essays, cartoons, and scripts to online and print publications, including and . His work often featured absurd, self-deprecating humor, such as essays exploring everyday absurdities and illustrated strips with comedic mishaps. These pieces helped establish his voice in the burgeoning internet humor scene, emphasizing concise, witty observations over traditional punchlines. Pinkerton launched jaypinkerton.com in the early as a simple portfolio showcasing his writing, cartoons, and artwork. Over time, it evolved into a dedicated platform for original humor content, hosting scripts, essays, and pieces like "Why I Probably Shouldn’t Do Stand-Up," which reflected on his comedic experiments. The site served as a central hub for his freelance output, attracting attention from editors and readers in the humor community before integrating with larger platforms.

Editorial roles at National Lampoon and Cracked

In the mid-2000s, Jay Pinkerton advanced from freelance contributions to a formal editorial position as of NationalLampoon.com, where he oversaw the production and curation of satirical content for the revived comedy brand's digital platform. His responsibilities included editing articles, coordinating with writers, and ensuring the site's alignment with National Lampoon's irreverent humor tradition, building on his earlier freelance work that had caught the attention of the publication. Around 2006, amid Cracked magazine's relaunch after a two-year hiatus, Pinkerton transitioned to an editorial role at and the accompanying print edition, serving as an editor during the site's resurrection as a major online humor destination. In this capacity, he contributed to both digital and print content, including authoring satirical pieces such as "Things I Learned in Prison (Rape-Related and Otherwise)," published in April 2007, which exemplified Cracked's blend of absurd and . Pinkerton's tenure at Cracked marked key achievements in expanding digital humor, including recruiting new talent and fostering collaborations that revitalized the platform during its early online growth phase from 2006 to 2008. Under his editorial guidance, evolved into a prominent site for list-based articles and spoofs, helping it compete in the burgeoning web comedy landscape by prioritizing crafted, shareable content over shock value alone.

Contributions at Valve Corporation

Jay Pinkerton joined in 2008 as a , drawn from his prior editorial role at where his humor writing had caught the attention of the studio. His early contributions focused on the series, where he helped craft narrative elements for the cooperative , released that same year. Pinkerton continued this work into the sequel, (2009), integrating story beats that enhanced the survivors' dynamics and environmental storytelling amid the . Pinkerton also provided extensive writing for , supporting its ongoing live-service model through narrative for numerous game updates, official comics, and animated shorts. Notable examples include his scripting of the animated short "Jungle Inferno," which tied into a major map update, and contributions to the comic series that expanded the game's lore around its class-based characters. These efforts helped maintain the game's humorous tone and community engagement over years of free content releases. His most acclaimed contribution came with (2011), where Pinkerton co-wrote the core story alongside and , building on the original game's puzzle-driven narrative. In developing characters, he emphasized deepening the antagonistic relationship between protagonist Chell and the AI GLaDOS, drawing from playtesting feedback to heighten their verbal interplay and emotional tension. Pinkerton also co-created , portraying the eccentric founder of Aperture Science as a brash, hands-on industrialist whose pre-recorded messages provided backstory and comic relief, contrasting the facility's sterile environment. This collaborative scripting earned widespread praise for its witty dialogue and cohesive plot. Pinkerton departed Valve in June 2017 after nearly a decade with the company.

Return to Valve and ongoing projects

After departing in June 2017, Pinkerton rejoined the company in July 2018, leveraging his prior decade-long tenure there to resume contributions in an undisclosed writing role. Upon his return, Pinkerton co-wrote the for Half-Life: Alyx, Valve's 2020 game set between the events of and , incorporating elements tailored to VR gameplay such as immersive environmental interactions and spatial to enhance player agency in the first-person perspective. He has since contributed writing to multiple Valve VR experiences, emphasizing narrative integration with virtual reality mechanics to create more intuitive and engaging user interactions. Pinkerton's ongoing work at includes additional content for , such as updates and expansions that build on the game's humor-driven lore, as well as scripting for animated shorts that expand the franchise's character backstories. In 2024, he co-wrote the seventh and final issue of the Team Fortress comics series with , titled "The Days Have Worn Away," which was released on December 20, 2024, and marks the conclusion of the ongoing narrative arc.

Notable works

Video game writing

Jay Pinkerton served as a co-writer on (2011), collaborating with and to expand the original Portal's intimate narrative into a broader story centered on the player's evolving relationship with , while introducing new characters like Wheatley and . His contributions included structuring the plot to balance puzzle-solving with character-driven progression, ensuring the single-player campaign's arcs—from awakening in stasis to confronting a facility takeover—built tension through escalating betrayals and revelations. Pinkerton focused on dialogue that humanized psychopathic AI entities, crafting lines for "idiotic, psychopathic machines" that relied on to convey without visual reliance, such as Wheatley's bumbling yet menacing banter. In integrating humor, Pinkerton and the team aimed for "belly laughs," transforming into a "video game comedy" by layering satirical jabs at corporate culture and scientific into the dialogue and environmental storytelling, exemplified by Cave Johnson's bombastic monologues that mocked Aperture Science's absurd history. This approach earned the game widespread acclaim for its witty script, with Pinkerton's background in humor writing enabling seamless fusion of with narrative momentum. Pinkerton's narrative work on the series (2008–2009) emphasized cooperative storytelling through dynamic survivor interactions and environmental cues, co-writing elements like the DLC comic The Sacrifice alongside to provide backstory on the survivors' desperate journey. He contributed to in-game dialogue systems that generated emergent narratives based on player actions, such as banter during hordes that highlighted group dynamics and tension. Environmental was woven into saferooms and , satirizing through ironic survivor notes and abandoned media, enhancing the co-op experience without a linear script. Pinkerton also provided developer commentary on features, like weapon upgrades, underscoring his role in tying narrative flavor to mechanics. For (2007–ongoing), Pinkerton handled extensive writing across comic series arcs, update stories, and animated shorts, often collaborating with to expand the game's lore beyond multiplayer chaos. He authored the six-part comic series starting with Ring of Fired (2013), developing multi-issue arcs that explored the mercenaries' backstories, corporate intrigue with the Mann brothers, and post-update events like the robot invasion in A Cold Day in Hell (2014). For the Mann vs. Machine update (2012), Pinkerton's writing introduced Gray Mann as a new through tied-in comic elements and in-game briefs, framing the co-op mode as a desperate defense against robotic hordes in a satirical take on . In shorts like (2014), he contributed to the script's humorous plot involving a bread-based apocalypse and character relationships, blending with lore hints like Scout and Miss Pauling's dynamic. These efforts, spanning over 40 updates and shorts, maintained narrative continuity while amplifying the game's chaotic humor. Pinkerton co-wrote the seventh and final comic issue, The Days Have Worn Away (2024), concluding the storyline with themes of and redemption. Pinkerton co-wrote the story for Half-Life: Alyx (2020) with and , adapting the Half-Life series' lore for by emphasizing immersive, first-person perspective shifts and environmental interaction. His contributions focused on resolving the "prequel problem," structuring the plot around Alyx Vance's five-year gap mission to craft a self-contained arc that advanced the overarching narrative without resolving broader mysteries. Key elements included the climactic twist where Alyx frees the G-Man, who grants a consequential favor by saving Eli Vance, re-energizing the resistance in a way tailored to VR's intimacy—"the idea that once you free god, god owes you a favor." Pinkerton preserved lore ambiguity, particularly the G-Man's alien nature, ensuring VR immersion heightened player investment in subtle details like Combine and personal stakes. This adaptation made the game feel pivotal, bridging past events while teasing future possibilities. Pinkerton also co-wrote (2022), a free short-form VR experience set in the Science , collaborating with on its comedic narrative involving desk work and portal gun mishaps. Jay Pinkerton's contributions to print and online humor span satirical essays, cartoons, and editorial work across magazines and websites, often focusing on absurd pop culture observations and everyday absurdities. As a senior editor at Cracked.com from 2006 to 2008, Pinkerton wrote and oversaw numerous articles blending investigative parody with dark humor. Notable examples include "St. Patrick's Day Exposed," a 2007 piece satirizing the holiday's myths and excesses through mock reporting. Similarly, "Things I Learned in Prison (Rape-Related and Otherwise)," published in April 2007, humorously dissects prison stereotypes and survival tips in a first-person narrative style. These articles exemplify his approach to taboo subjects with witty exaggeration, contributing to Cracked's revival as a digital humor outlet. He also edited print issues of Cracked magazine during this period. Earlier in his career, Pinkerton contributed freelance pieces to National Lampoon's website, where he advanced to , curating satirical content on contemporary culture. His online portfolio at jaypinkerton. archived original essays and cartoons, including the 2006 self-deprecating reflection "Why I Probably Shouldn't Do Stand-Up," which chronicles awkward attempts at live comedy and the pitfalls of aspiring performers. The site functioned as a central hub for his non-magazine work, showcasing short satirical sketches and illustrations that later influenced his editorial roles. Pinkerton's essays on pop culture tropes appeared on platforms like .com, where he explored themes such as media clichés and social awkwardness in bite-sized formats. His print contributions extended to Jest Magazine, featuring humorous short pieces, and Best Non-Required Reading 2003, which included selected satirical writings. These outlets highlighted his concise, observational style, bridging freelance humor with established publications.

References

  1. https://www.pcgamer.com/jay-pinkerton-leaves-valve-as-it-continues-shedding-writers/
  2. https://gothamist.com/arts-entertainment/jay-pinkerton-humorist-editor-of-cracked-magazine
  3. https://www.cracked.com/members/jay-pinkerton_contributor
  4. https://variety.com/2018/gaming/news/jay-pinkerton-back-at-valve-1202889650/
  5. https://www.thegamer.com/half-life-alyx-ending-explained-writers/
  6. https://www.valvesoftware.com/en/people
  7. https://www.uploadvr.com/valve-more-half-life/
  8. https://rocketreach.co/jay-pinkerton-email_22729595
  9. https://thedailyomnivore.net/2010/11/09/jay-pinkerton/
  10. https://www.adweek.com/performance-marketing/michael-ian-black-named-editor-at-large-as-cracked-returns-from-2-year-hiatus/
  11. https://www.cracked.com/article_14853_things-i-learned-in-prison-rape-related-otherwise.html
  12. https://gameinformer.com/2018/07/30/portal-2-co-writer-jay-pinkerton-returns-to-valve
  13. https://www.pcgamer.com/portal-2-co-writer-jay-pinkerton-seems-to-be-back-at-valve/
  14. https://www.eurogamer.net/portal-2-co-writer-jay-pinkertons-back-at-valve
  15. https://wiki.teamfortress.com/wiki/Jay_Pinkerton
  16. https://www.ign.com/articles/2017/06/07/jay-pinkerton-becomes-the-fourth-valve-writer-to-leave-in-two-years
  17. https://nationalpost.com/arts/qa-with-portal-2-writers-erik-wolpaw-and-jay-pinkerton
  18. https://www.eurogamer.net/portal-2-lets-make-caddyshack-interview
  19. https://www.rockpapershotgun.com/valve-loses-its-fourth-writer-in-two-years-as-jay-pinkerton-leaves-the-company
  20. https://www.polygon.com/2020/4/10/21212241/half-life-alyx-ending-explained-discussed-g-man-gordon-freeman-half-life-3
  21. https://www.gamesradar.com/comics/7-years-since-its-last-issue-the-official-team-fortress-2-comic-is-officially-back-from-the-dead-with-a-completed-script/
  22. https://wiki.teamfortress.com/wiki/The_Days_Have_Worn_Away
  23. https://www.mobygames.com/person/348983/jay-pinkerton/
  24. https://left4dead.fandom.com/wiki/Developer_Commentary_%28Left_4_Dead_2%29
  25. https://www.linkedin.com/in/jay-pinkerton-1b65352
  26. https://www.teamfortress.com/comics.php
  27. https://tvtropes.org/pmwiki/pmwiki.php/Webcomic/TeamFortress2
  28. https://www.teamfortress.com/tf07_thedayshavewornaway/
  29. https://combineoverwiki.net/wiki/Jay_Pinkerton
  30. https://www.polygon.com/2020/4/10/21212241/half-life-alyx-ending-explained-discussed-g-man-gordon-freeman-half-life-3/
  31. https://combineoverwiki.net/wiki/Aperture_Desk_Job
  32. https://www.cracked.com/article_14972_st.-patricks-day-exposed.html
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