Suzanne Hanover/Universal Judd Apatow'sThe 40-Year-Old Virginstars Steve Carell as an aging electronics store worker desperate to finally score. The raunchy romantic comedy hit theaters on Aug. 19, 2005. The star-studded cast includes Catherine Keener, Paul Rudd, Seth Rogen, and Jane Lynch. WhenThe 40-Year-Old Virginhit theaters 20 years ago this month, it helped usher in a new wave of R-rated comedies while introducing audiences to some of the most ubiquitous film and TV stars of this century. The directorial debut of acclaimed writer and producerJudd Apatow, the film follows Andy Stitzer (Steve Carell), an electronics store employee who, as the title implies, is a 40-year-old virgin. Determined to change that, his crude coworkers make it their mission to find him a partner. To celebrate its 20th anniversary,The 40-Year-Old Virginis returning to theaters for a special one-week run starting Aug. 22. To honor this milestone, we're catching up with the hilarious cast ofThe 40-Year-Old Virginto see how their lives and careers have unfolded over the last two decades. 01 of 12 Suzanne Hanover/Universal; Unique Nicole/WireImage Steve Carell was already a comedic force thanks to his turns onThe Dana Carvey Show(1996),The Daily Show(1999–2005), and as Brick Tamland inAnchorman(2004), but it wasThe 40-Year-Old Virginthat gave him his first leading role. At a20th anniversary screeningthis past May, Carell reflected on his time making the film, calling it "pure fun, all the way through." He added, "To have a job where you know, every day when you go to work you are going to laugh until you cry every single day, is such a gift." Carell went on to establish himself as a household name as the beloved Michael Scott onThe Office(2005–2011, 2013), on which he starred, wrote, produced, and directed. He kept the laughs coming in films likeEvan Almighty(2007),Get Smart(2008),Date Night(2010),Crazy, Stupid, Love(2011), and of course, as the voice of Gru in theDespicable Mefranchise (2010–present). But the actor has since sought to push the boundaries of his persona, taking on dramatic roles and even getting an Oscar nomination for his performance inFoxcatcher(2014). He chased that role with weightier turns inThe Big Short(2015),Battle of the Sexes(2017),Vice(2018), andThe Morning Show(2019–2021), the latter of which earned him an Emmy nod. Most recently, he starred alongside Tina Fey on Netflix'sThe Four Seasons(2025) and appeared in HBO'sMountainhead(2025), a blistering satire fromSuccessioncreator Jesse Armstrong. 02 of 12 Suzanne Hanover/Universal; Monica Schipper/Getty Catherine Keenerplayed Trish, the charming single mom who wins Andy's heart inThe 40-Year-Old-Virgin. By the time the film hit theaters, Keener was already an Academy Award nominee forBeing John Malkovich(1999). She earned her second Oscar nomination for playingTo Kill a Mockingbirdauthor Harper Lee inCapote(2005) and continued to mix prestige and fun with roles inInto the Wild(2007),Get Out(2017), and theJim Carrey-led seriesKidding(2018–2020). Most recently, she played Arthur Fleck's (Joaquin Phoenix) lawyer inJoker: Folie à Deux(2024). 03 of 12 Suzanne Hanover/Universal; Dimitrios Kambouris/Getty Is it even a comedy ifPaul Rudd's not in it? By the timeThe 40-Year-Old Virginpremiered, Rudd had already built a solid filmography (and a reputation for not aging). He'd just worked with Carell and Apatow onAnchorman, and it seems he wanted to continue that collaboration. The Rudd–Apatow bromance only grew stronger, leading to more collaborations withKnocked Up(2007),Forgetting Sarah Marshall(2008) andThis Is 40(2012). Rudd's kept the comedy gold coming with roles inRole Models(2008),I Love You, Man(2009),Ghostbusters: Afterlife(2021), and this year'sFriendship. In 2015, he put on a superhero suit and became Marvel's tiniest Avenger inAnt-Man. He's made several appearances in the MCU since then, and he's set to return in next year'sAvengers: Doomsday. 04 of 12 Suzanne Hanover/Universal; John Sciulli/Getty Romany Malcowas looking to pivot from music to acting when he landed the role of Jay inThe 40-Year-Old Virgin.Since then, he's appeared in a number of films, includingBlades of Glory(2007),Think Like a Man(2012),The DUFF(2015), andHoliday Rush(2019). He's carved out a solid TV career, too, with leading roles onWeeds(2005–2008, 2012),No Ordinary Family(2010–2011), and the ABC tearjerkerA Million Little Things(2018–2023), on which he starred for five seasons. In a 2020 chat withYahoo, Malco admitted that he begged Apatow to cut him out of the movie. "I was like, 'My mom is an ordained minister, bro, cut me out of the movie, please. I'm serious.' I was like, 'Just cut my behavior,'" he recalled. Apatow refused, per Malco, telling the actor, "We can't. You're funny." 05 of 12 Suzanne Hanover/Universal; Earl Gibson III/Deadline via Getty Seth Rogen's been a consistent presence in Hollywood since his breakout onFreaks and Geeks(1999), where he first teamed up with Apatow, an executive producer on the cult comedy. By the timeThe 40-Year-Old Virgincame around, Rogen was well on his way to becoming one of comedy's most recognizable faces (and voices). As a writer and producer, Rogen's delivered a number of enduring comedies, fromSuperbad(2007) andPineapple Express(2008) toThis Is the End(2013), which he co-directed alongside longtime creative partner Evan Goldberg. Along with his comedic roles, Rogen has dabbled in drama with turns in Danny Boyle'sSteve Jobs(2015) and Steven Spielberg'sThe Fabelmans(2022), as well as the Hulu miniseriesPam & Tommy(2022), which nabbed him Emmy nominations for acting and producing. Most recently, he's returned to his comedy roots by starring on the Emmy-nominatedThe Studio, which he co-created with Goldberg. At a red carpet event forThe Studiothis past May, Rogen toldPEOPLEthatThe 40-Year-Old Virgin "was the first movie that I was a part of that I really had a creative voice in, and a lot of the R-rated humor and tone came from me really advocating for that." 06 of 12 Suzanne Hanover/Universal; Rodin Eckenroth/Getty Elizabeth Banksplayed wild child Beth inThe 40-Year-Old Virgin, and she soon became a pop culture staple thanks to her turns onScrubs(2006–2009),The Hunger Gamesfranchise (2012–2015), and thePitch Perfectfilms (2012-2017). Lately, she's been working behind the scenes, making her feature directorial debut withPitch Perfect 2(2015) before helmingCharlie's Angels(2019) andCocaine Bear(2023). Up next for Banks is a starring and producing role on the psychological thrillerDreamQuilwith John C. Reilly. She'll also star in the Peacock seriesThe Miniature WifealongsideSuccessionstar Matthew Macfadyen. 07 of 12 Universal/Courtesy Everett; Jamie McCarthy/WireImage Leslie Mannbrought total party girl energy as Nicky inThe 40-Year-Old Virgin, and she's been popping up in more comedies ever since. She's starred in several Apatow comedies —Funny People(2009),This Is 40(2012),The Bubble(2022) — which tracks since they've been married since 1997. Outside the Apatow-verse, you might have seen her in fan-favorite films like17 Again(2009),The Bling Ring(2013), andBlockers(2018). Next, she'll appear inPoetic License(2025), the feature directorial debut of her and Apatow's eldest daughter,Maude. 08 of 12 Universal; Michael Buckner/Variety via Getty Five-time Emmy winnerJane Lynchmight be one of be the hardest-working people in comedy. After stealing scenes as Andy's wildly inappropriate boss inThe 40-Year-Old Virgin, she's popped up in hit after hit. You might recognize her from films likeTalladega Nights(2006),Role Models(2008), andRalph Breaks the Internet(2018), but TV is where she reigns supreme, with her Emmy-winning turn as Sue Sylvester onGlee(2009–2015) standing out as a highlight. But Lynch has slayed on dozens of different series, fromTwo and a Half Men(2004–2014) andParty Down(2009–2010) toThe Marvelous Mrs. Maisel(2017–2023) andOnly Murders in the Building(2021–2024). 09 of 12 Suzanne Hanover/Universal; Jon Kopaloff/Getty At the 20th anniversary screening ofThe 40-Year-Old Virgin,Kat Denningsshared that it was one of her very first big gigs. If you recall, she played Trish's angsty teen daughter, Marla. Flash forward and Dennings has carved out an impressive career. You probably know her best as Max on2 Broke Girls(2011–2017) or as Darcy Lewis from Marvel projects likeThor(2011),WandaVision(2021), andWhat If...?(2021–2024). Dennings currently produces and stars on the ABC sitcomShifting Gears(2025) with Tim Allen. 10 of 12 Universal; Emma McIntyre/WireImage Mindy Kalingplayed David's ex, Amy, inThe 40-Year-Old Virgin. It was a small role, but it kicked off what's now one of the brightest careers from that cast. She worked alongside Carell onThe Office, starring as Kelly Kapoor and also writing for the hit NBC series. From there, Kaling skyrocketed to fame by creating, producing, and starring onThe Mindy Project(2012–2017). She's also the creator of shows likeNever Have I Ever(2020–2023),The Sex Lives of College Girls(2021–2025), andRunning Point(2025–present). 11 of 12 Universal; Steve Granitz/FilmMagic Gerry Bednob made quite the impression inThe 40-Year-Old Virginas Mooj, the foul-mouthed coworker who gives Andy some colorful sex advice. Since then, he's reunited with Rogen and Banks forZack and Miri Make a Porno(2008), and also appeared inThe Lie(2011) andBarb and Star Go to Vista Del Mar(2021). At the 20th anniversary screening, Bednob revealed that fans ofThe 40-Year-Old Virginstill come up to him to quote his outrageous lines and ask how much actually came from the script. The filthiest gems, he said, were all his. 12 of 12 Universal; Jerod Harris/Getty Shelley Malil played Haziz, one of Andy's coworkers at the electronics store inThe 40-Year-Old Virgin. Before and after the film, he appeared in supporting roles across TV and film, with appearances onReba(2007) andColumbus Day(2008). However, Malil's career came to a halt in 2008 after he was arrested and later convicted of attempted premeditated murder and assault with a deadly weapon afterstabbing his then-girlfriend 20 times. In 2010, he wassentenced to life in prisonwith the possibility of parole. Malil wasreleased on parolein 2018. Since then, he has remained out of the public eye. The 40-Year-Old Virginiscurrently available to stream on Prime Video. Want more movie news? 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