Judd Apatow’s 50 Best Characters, Ranked

The reigning king of comedy turns 50 today. Let’s celebrate.

December 6, 2017 9:00 am

Some well wishes are in order.

Fifty years ago today, Judd Apatow — the man responsible for approximately half of all American laughs since 2005 — was born.

In the half-century since, he’s built up a comedic CV nearly as long as Funny People.

You’ve got the romantic dramedies that made him a household name: The 40-Year-Old Virgin, Knocked Up, Superbad. The beloved TV series: Freaks and Geeks, Undeclared. Even a couple wonky, uncredited rewrites: Happy Gilmore, Bruce Almighty.

What makes the Apatow oeuvre so appealing is its familiarity: his films leave behind the gross-out gags and cartoonish characters of the late ‘90s and early aughts (think American Pie, Road Trip, those tiresome Not Another … films) in favor of relatable characters forced to navigate real-world problems: stale marriages, small-town malaise, a one-night stand gone awry.

So in his honor, we’ve decided to cobble together a ranking of his 50 greatest characters — one for each year of his life.

A few notes on our methodology:

Given Apatow’s ubiquity, he’s co-produced work with some of the biggest names (Will Ferrell, Adam McKay, David Wain, Lena Dunham) in comedy over the years. And while projects like Step Brothers, Anchorman and Girls are indicative of Apatow’s penchant for success, can we really say they’re examples of his unique brand of scruffy, sensitive, self-deprecating humor? Not exactly.

So don’t expect to find Hannah Horvath or the Channel 4 News Team on this list. Expect, instead, to find the pothead, the fanatic, the last guy chosen for kickball and the in-over-their-heads newlyweds. Not to mention all the developmentally arrested sidekicks, cameos and bit parts who supplied some of Apatow’s most quotable lines.

Enjoy the cake, Judd. Here’s hoping it has trick candles.

1. Peter (Jason Segel) — Forgetting Sarah Marshall
We tend to collectively fetishize movie stars and the characters they play. Give Americans a swashbuckling he-man or brooding tough guy as a role model, and they’ll grow up thinking that violence solves problems and sensitivity is a fatal flaw. Which brings us to Peter Bretter, a heartbroken TV theme producer who flouts the conventions of the traditional leading man at every turn. Peter cries. Peter is afraid of heights. Peter mopes after breakups. And yet, unlike Steve Carell’s 40-Year-Old Virgin, Peter is also someone men want to emulate: a romantic, self-deprecating dreamer with a plan that involves puppets, Dracula and musical theater.

At a time when masculinity is in serious need of renovation, we need more Peter Bretters in Hollywood. And Judd Apatow is leading the charge to make sure that happens.

2. Fogell/McLovin (Christopher Mintz-Plasse) — Superbad
Aristotle. Beyoncé. McLovin? If not in the pantheon of mononyms, McLovin’s got a comfortable armchair in the lobby. That name means something. When we meet him, he is merely Fogell, interrupting Home Ec with those famous “Gangstas!, the kind of guy you’ve given up on trying to unfriend. But 80 minutes later? He’s lighting up the police cruiser with Officers Slater and Michaels, being dragged out of house parties and no longer a virgin (kind of). It’s an all-time cinematic apotheosis.

3. Annie (Kristen Wiig) Bridesmaids
Even before Bridesmaids, Kristen Wiig’s brilliance was undeniable. But with Annie, she was able to really show her stuff, outdoing Melissa McCarthy’s slapstick (drunk on the airplane beats sh*tting in the sink) with a deft touch that often mashes genuine sadness and laugh-out-loud gags into the same scene. She also got an Oscar nod for co-writing the damn thing.

4. Seth (Jonah Hill) — Superbad
Everyone had a friend like Seth growing up. And if you didn’t, that sucks. Sure, he’s a got a mouth like an internet-surfing sailor, wields peer pressure like a blade and can’t be trusted when pizza bagels are involved. But he’s funny as all hell and his heart is, generally, in the right place. Great artist as well.

5. Saul Silver (James Franco) — Pineapple Express
Saul — who sells pot to keep his grandmother in a nice retirement home and dreams of becoming a civil engineer “who designs septic tanks for playgrounds” — is proof that even the least believable, most broadly written characters in any Apatow-family film possess both humor and pathos. Personal note: at a screening during the movie’s first week out, the argument between Dale (Seth Rogen) and Saul — where the duo briefly split and Saul is left crying and sad eating on a, natch, playground swing — elicited a unironic audience “aww.”

6. Rachel (Mila Kunis) — Forgetting Sarah Marshall
Mila Kunis’s turn as a boisterous, flower-over-the-ear ex-Mainlander with an ear for sarcasm is pretty much the rebound of the century for Segel’s Peter Bretter. The character easily could’ve veered into manic pixie dream girl territory, but Rachel’s bullshit meter, ferocity and uneasy relationship with her own past elevate her beyond the station of some despondent schmuck’s timely love interest.

7. Evan (Michael Cera) — Superbad
In the final scene of Superbad, Seth and Evan part ways arm-in-arm with their respective crushes. And even then, achievement unlocked, they can’t help but stare back at each other as they walk into the sunset. For all their talk of the things they need — Goldslick vodka, hooking up, getting into the right school — it’s companionship that got them through their blunder years. And as far as friends go, they don’t come any more loyal than Evan.

8. Aldous Snow (Russell Brand) — Forgetting Sarah Marshall, Get Him to the Greek
The role Russell Brand was born to play. Twice. Aldous Snow is a gyrating, umpteen-years-sober boudoir yogi prone to rants on lost flip flops, the fluidity of relationships and the meaning of life. But really, somewhere not too far past the surface … he is patently full of sh*t. Brilliant.

9. Bill Haverchuck (Martin Starr) — Freaks and Geeks
This show has been touted as the launching pad of James Franco, Seth Rogen and Jason Segel, but it’s Martin Starr’s gangly, four-eyed Bill Haverchuck you’ll be quoting after rewatching the 18 episodes — especially his devastating prank phone call. His telescopic lenses and geriatric gesticulations paint him as a classic geek, but he’s the show’s true catalyst: throwing his dweeb team in the mix with the cool kids through feats of bravery like commandeering the baseball team and swapping a keg with non-alcoholic beer (then drinking the loot).

10. Paula (Jane Lynch) — The 40-Year-Old Virgin
Jane Lynch — a tour de force in most roles she plays — has never been better than as Steve Carell’s handsy, leering, gender-role-flipping manager at Smart Tech. Free lesson in unwelcome propositioning: “Ever heard of the term ‘f*ck buddy’?”

11. Kunu (Paul Rudd) — Forgetting Sarah Marshall
As a 44-year old surfing instructor, Paul Rudd embodies the “clueless male” trope in a positive light. Admittedly, you don’t want a lot of Kunu in your life, but when he pops up, do listen: He’s offering you hope. And … well, not wisdom, but a message you’ll remember nonetheless.

12. Megan (Melissa McCarthy) — Bridesmaids
13. Officers Slater and Michael (Bill Hader, Seth Rogen) — Superbad
14. Red (Danny McBride) — Pineapple Express
15. Jay (Romany Malco) — The 40-Year-Old Virgin

16. Kumail (Kumail Nanjiani) — The Big Sick
It’s a classic Apatow romantic comedy setup: sardonic everyman who drives an Uber and loves The X-Files meets an equally sardonic young woman at a comedy club. They have a quirky, endearing courtship. And then (spoiler), she gets really sick. But, interestingly, this is no product of the school of Apatow — it’s based on Nanjiani’s real-life relationship with his wife.

17. Andy (Steve Carell) — The 40-Year-Old Virgin

18. Club Doorman (Craig Robinson) — Knocked Up
This is how you steal a scene:

19. LeBron James (Himself) — Trainwreck
Relationship advisor, pick-up basketball buddy and frequent lunch companion to Bill Hader’s Dr. Aaron Conners? No Jordan whataboutism here. LeBron is the greatest basketball player of all time … to appear in an Apatow film.

20. Aaron (Jonah Hill) — Get Him to the Greek
21. Brian and Liz (Bill Hader and Liz Cackowski)  — Forgetting Sarah Marshall
22. George Simmons (Adam Sandler) —
Funny People

23. Lindsay Weir (Linda Cardellini) — Freaks and Geeks
In a show full of caricatures — even her dopey brother Sam lays it on a little thick — Linda provides the rare, nuanced mirror to reflect the viewer’s own high-school experience, as well as the best meme to come from the series.

24. School Liaison Officer (Cleo King) — Pineapple Express
In a movie full of crooked cops, this noble officer just wants to protect her students from shady narcotics dealers.

25. Matthew the Waiter — Forgetting Sarah Marshall
A GIF machine in a pre-GIFs world. “I’ll just go f*ck myself … Mahalo!”

26. Ira (Seth Rogen) — Funny People
27. Neal Schweiber (Samm Levine) — Freaks and Geeks
28. Francis the Driver (Joe Lu Truglio) — Superbad
29. Mooj (Gerry Bednob) — The 40-Year-Old Virgin
30. Debbie (Leslie Mann) — Knocked Up

31. eBay Customer (Jonah Hill) — The 40-Year-Old Virgin
That murmured “Congratulations” … Hill’s cameo as a beanied, barely-there bystander who doesn’t understand the concept of Catherine Keener’s eBay Store is never not funny.

32. John Cena (Himself) — Trainwreck

33. Mickey Dobbs (Gillian Jacobs) — Love
One of the early criticisms of Judd Apatow was that his female characters tended to lack depth. OK, they’re foils to the sad-sap male characters we love, but what else? Where are their rich inner lives and dreams and personal histories? Like Wiig’s Annie in Bridesmaids, Mickey reverses this trend. She’s a crass, free-wheeling, cynical twentysomething, and given the longer format of a TV series, she has the space to truly grown and flourish.

34. Harold Weir (Joe Flaherty) — Freaks and Geeks
35. Daisy (Aubrey Plaza) — Funny People
36. Sergio (Sean Combs) — Get Him to the Greek

37. Cain (David Cross) — Year One
The finest moment in a film that could easily have never been made: Cain bludgeoning brother Abel (Paul Rudd) to death with a rock. “What have I done?” Abel wakes up. Hits him again. “What have I continued to do?”

38. Nikki (Vanessa Bayer) — Trainwreck
Other actors are praised for the amount of emotion they can convey without even opening their mouth. Bayer can be oppositely applauded: for how quickly she makes people laugh simply by opening her mouth.

39. Darald (Jack McBrayer) — Forgetting Sarah Marshall
40. David (Paul Rudd) — The 40 Year-Old-Virgin
41. Mark Taylor Jackson (Jason Schwartzman) — Funny People
42. Dr. Lars (Torsten Voges) — Funny People

43. Sadie and Charlotte (Maude and Iris Apatow) — Knocked Up
Should we be surprised that the daughters Apatow were freakishly talented comedic actors pretty much out of the womb?

44. Rose Byrne (Jackie Q) — Get Him to the Greek
45. Rita (Wendy McLendon-Covey) — Bridesmaids
46. Randy (Aziz Ansari) — Funny People

47. Jess (Lauren Lapkus) — Crashing
“F*ck that false puritanical bullshit. It’s not about that. God is everywhere, okay? God was in the restaurant when you were frenching your mom. He’s in the weed. He’s in everything.” If a woman leaves your uptight life to find herself, let it be an angry, stoned Lauren Lapkus. It’s for your benefit.

48. Boy at Health Clinic  (Loren Berman) — The 40 Year-Old-Virgin
“You’d tap that? What, Seth, you think you’re cool with your little Jew fro?”

49. Coach Fredricks (Thomas Wilson) — Freaks and Geeks
It’s Biff Tannen as an affable high school gym teacher forced to teach sex-ed. C’mon.

50. Michael McDonald (Himself … kind of) — The 40-Year-Old Virgin
“If I hear ‘Yah Mo B There’ one more time, I’m gonna ‘Yah Mo’ burn this place to the ground.” Despite Paul Rudd’s protests, Michael McDonald played and played … all way the way onto this list. It’s Apatow’s greatest cameo, and he never even had to step on set.

Additional reporting by Alex Lauer, Danny Agnew, Evan Bleier, Kirk Miller and Walker Loetscher

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