From 'The 40-Year-Old Virgin' to 'Trainwreck,' the 9 Best Judd Apatow Movie Cameos

Gwynne Watkins
Writer, Yahoo Entertainment
Yahoo Movies

What do Kristen Wiig, Elizabeth Banks, and Ken Jeong have in common? Well, they’re all very funny — and they all got their big break in movies thanks to a cameo in a Judd Apatow film. Beginning with his big-screen directorial debut The 40-Year-Old Virgin in 2005, Apatow has always taken opportunities to feature up-and-coming comedic talent — or to show off established stars (like Eminem) in an unexpected light. Here, from The 40-Year-Old Virgin to the currently-in-theaters Trainwreck, are the best featured cameos from a decade of Judd Apatow joints. (Warning: The clips contain some NSFW language.) 

Kristen Wiig and Alan Tudyk in Knocked Up (2007)
Wiig was still a relatively unknown Saturday Night Live cast member when she floored audiences with a two-minute scene in Knocked Up. (Watch it below.) As Jill, a cable executive who reluctantly promotes producer Alison (Katherine Heigl) to on-air reporter, Wiig gives a master class in passive-aggression. “We don’t want you to lose weight,” she assures Alison. “We would just like it if you go home, and step on the scale, and write down how much you weigh, and subtract it by, like, 20. And weigh that much.” The enthusiasm for Wiig’s Knocked Up cameo led directly to her collaboration with Judd Apatow on Bridesmaids, but we should note that she didn’t steal this scene alone: The reliably funny Alan Tudyk (playing, literally, the Jack to her Jill) is a perfect comic foil.

Leslie Jones in Trainwreck (2015)
SNL actress Leslie Jones is credited only as Angry Subway Patron in Trainwreck, but she puts some of the movie’s bigger-name cameos to shame. (Matthew Broderick, we’re looking at you.) In Jones’ short but memorable scene, Amy (Amy Schumer) asks the future Ghostbusters star why their subway train has stopped. She reels off a logical answer, then angrily reveals that she made it up, because what subway passenger ever knows why the trains stop? It’s a moment no Metrocard carrier is likely to forget.

Melissa McCarthy in This is 40 (2012)
After watching her shoot Bridesmaids, Apatow gave McCarthy a cameo in his next film, This is 40.  McCarthy’s turn as Catherine, the mother of a boy who has been harassing Paul Rudd and Leslie Mann’s teenage daughter, is the funniest thing in the movie. In a principal’s office scene partially improvised by McCarthy (watch it below), Catherine becomes increasingly incensed at Rudd and Mann, calling them a “bulls— bank commercial couple” and threatening to chew through them like a rat. In a final coup de grace, she turns her ire on the mild-mannered principal. (“This is why everybody hates you, Jill!”) The scene is such a show-stopper that Apatow elected to play the blooper reel — in which Mann and Rudd literally cry with laughter, but McCarthy never breaks — over the end credits.

Leslie Mann in The 40-Year-Old Virgin (2005)
Sure, we all know now that Leslie Mann is Judd Apatow’s wife. But when The 40-Year-Old Virgin first hit theaters, we only knew she was a riot. Mann plays Nicky, a bachelorette-party attendee whom sexually inexperienced Andy (Steve Carell) attempts to seduce. In her five minutes onscreen, Nicky transitions from cute drunk to full-on hot mess, bashing her car into passersby while singing along to Missy Elliott and growling “Let’s get some f—ing French toast!” before vomiting daiquiris all over poor Andy.

Eminem and Ray Romano in Funny People (2009)
Obviously, Apatow gave neither of these people their big break — but he did make their worlds collide in Funny People, with rib-tickling results. Both stars play themselves, as attendees at a party thrown by George (Adam Sandler) to celebrate his cancer-free status. (Watch the scene below.) The rapper begins to deliver a morose monologue about how much he hates fame (“I can’t go to f—ing Chuck E. Cheese, I can’t go to Target, I can’t go to Best Buy…”), then unleashes a verbal tirade on Romano for staring at him from across the restaurant. “This is why I don’t go out of the house,” mutters the sitcom star.

Ken Jeong in Knocked Up (2007)
The part of Dr. Kuni wasn’t written for Ken Jeong, but it might as well have been: Apatow was looking for “an Asian actor with medical experience,” and the doctor-turned-comedian fit the bill. Jeong made his film debut as the short-fused OB-GYN who scoffs at Katherine Heigl’s “all natural” birth plan, advising her, “If you want a ‘special experience,’ go to a Jimmy Buffet concert.”

Keith Robinson in Trainwreck (2015)
Continuing his tradition of giving lesser-known comedians a big-screen break, Apatow gives stand-up comic Keith Robinson a choice film debut in Trainwreck. Robinson plays a movie theater patron who gets into an argument with Amy’s musclebound boyfriend (John Cena), only to become confused when Cena’s threats seem oddly sexual in nature. History goes to show that a good Apatow cameo can lead to bigger things — so it might be time for Robinson to put a photo on his IMDb page.

Elizabeth Banks in The 40-Year-Old Virgin (2005)
One of the roles that put Banks on the map was her raunchy performance as Beth, the sweet bookstore employee who unleashes her kinky side when she takes Andy (Steve Carell) home. Her first scene — in which she unknowingly helps Andy with his first successful flirtation — was entirely improvised. (Watch it below.) But it’s a later moment, involving a bathtub and a handheld shower head, that really made audiences take notice.

James Taylor in Funny People (2009)
Because hearing the soulful singer-songwriter cuss out Facebook was worth the price of a movie ticket.