The Best (and Worst) of Judd Apatow: His Films Ranked

Since the early 2000s, Judd Apatow has been responsible for some of the funniest films of the modern era. From producing films like Anchorman: The Legend of Ron Burgundy and Superbad to his own directorial efforts, Apatow remains one of the biggest names in big-screen comedy working today. This year, he has a number of high-profile projects on the way, including a collaboration with The Lonely Island and Pee-Wee’s Big Holiday. Here’s our definitive ranking of his work as director.

5. Funny People (2009)

Adam Sandler and Seth Rogen in Funny People

Source: Universal Pictures

The lowest-grossing film on Apatow’s resume, Funny People stars Adam Sandler as a comedian who is diagnosed with a terminal health condition. If that premise doesn’t immediately inspire laughter, it’s probably because — despite its focus on stand-up comics — Funny People is far more of a drama than anything else. Despite solid performances across the board, the film clashes tonally and never truly soars as either a comedy or drama. Though some saw it as Apatow’s most mature film up to that point, many viewed it as a step backward following back-to-back hits.

4. This Is 40 (2012)

Leslie Mann and Paul Rudd in This Is 40

Source: Universal Pictures

Billed as a “sort of sequel to Knocked Up,” this spinoff centers on that film’s supporting characters, and admirably led by Leslie Mann and Paul Rudd, it serves as a natural expansion of Apatow’s exploration of relationships and the institution of marriage. Though This Is 40 blends comedy and drama more successfully than Funny People, the film’s narrative lacks focus at times and is more of a thematic meditation than it is a true tale of its central characters. In any case, enough laugh-out-loud moments manage to carry it along, including a memorable cameo role for Melissa McCarthy.

3. Trainwreck (2015)

Amy Schumer and Bill Hader in Trainwreck

Source: Universal Pictures

Until this comedy, Apatow had never directed a film he hadn’t written himself. Perhaps that’s why his collaboration with writer/star Amy Schumer is his best work in years. As a 30-something terrified of monogamy, Schumer brings the same incisive wit to her romantically challenged character as she does to her Comedy Central series Inside Amy Schumer. Coupled with Apatow’s skill for injecting heart into his comedies, the actress delivers a breakthrough performance that instantly launched her film career, and thanks to a gifted supporting cast that includes Bill Hader, LeBron James, John Cena, and Brie Larson, Trainwreck overcomes its flaws to become anything but what its title suggests.

2. Knocked Up (2007)

Seth Rogen and Katherine Heigl in Knocked Up

Source: Universal Pictures

Only Apatow’s second film, Knocked Up is that rare romantic comedy that plays equally well to both male and female audiences. When career woman Alison (Katherine Heigl) drunkenly hooks up with stoner Ben (Seth Rogen), the mismatched couple finds themselves unexpectedly expecting. Although its setup isn’t particularly ground-breaking, Apatow wrings such heart and insanely relatable laughs out of the story and his brilliant cast that the film remains his biggest box office hit almost a decade later. Too bad Heigl so publicly derided the film following its success.

1. The 40-Year-Old Virgin (2005)

Steve Carell and Elizabeth Banks in The 40-Year-Old Virgin

Source: Universal Pictures

Fans may find it hard to believe that Apatow’s first project in the director’s chair is still his very best. The film launched Steve Carell’s movie career, as the actor takes center stage as the titular Andy. Even more impressively, it’s filled with pitch-perfect casting all-around, from Seth Rogen, Paul Rudd, and Romany Malco’s roles as Andy’s co-workers/friends to Catherine Keener as the woman who ultimately wins Andy’s heart. The film’s title may imply nothing but crude humor regarding its protagonist’s lack of sexual experience (admittedly, there is some of that), but the film is far more poignant and surprisingly sweet than it has any right to be. Truly, The 40-Year-Old Virgin is a comedy that only grows more meaningful and hilarious with each viewing.

Follow Robert Yaniz Jr. on Twitter @CrookedTable

Check out Entertainment Cheat Sheet on Facebook!       

More from Entertainment Cheat Sheet: