The parameters are vague, of course, because most films do not fall into a single genre but contain elements of many. Some of these titles steep into the dramatic variety, while others are nothing more than 100 minutes of stupid, diverting fun. They all, however, keep the humor at the forefront. I haven’t included any of Charlie Kaufman’s films, because the melancholy generally overpowers the laughs (for me, at least). Comedy is unpredictable and subjective. I don’t understand, for example, why I find Anchorman hilarious but do not get the same experience from the equally nonsensical Zoolander (and forgive me but I never warmed to the Austin Powers franchise). I think the key is to find the people you like and stick with them. Full disclosure: There is a lot I haven’t seen, so I’m open to suggestions.
1. Annie Hall (1977) (Director: Woody Allen; Writer: Woody Allen, Marshall Brickman). Poignant, intelligent, and consistently funny, Annie Hall became a classic for a very valid reason.
2. Some Like It Hot (1959) (Director: Billy Wilder; Writer: Billy Wilder, I.A.L. Diamond). Jack Lemmon is brilliant in this fast-paced comedy of masquerade.
3. Sideways (2004) (Director: Alexander Payne; Writer: Alexander Payne, Jim Taylor). It might be more sour than sweet, but there’s wittiness even in the darker moments. Combine broad shenanigans with behavioral truth and you get a comedic titan.
4. The Big Lebowksi (1998) (Director: Joel and Ethan Coen; Writer: Joel and Ethan Coen). Jeff Bridges, along with the Coens, have created one of the most indelible personalities in modern cinema. The Dude abides.
5. Borat: Cultural Learnings of American for Make Benefit Glorious Nation of Kazakhstan (2006) (Director: Larry Charles; Writer: Sacha Baron Cohen, Anthony Hines, Peter Baynham, and Dan Mazer). Impossibly, indescribably, and uproariously funny. Sacha Baron Cohen has scary talent and no hint of shame or restraint.
6. Knocked-Up (2007) (Director: Judd Apatow; Writer: Judd Apatow). It’s not always trying to be a laugh-a-minute riot, but this film is nothing if not hilarious. It plays perfectly to Seth Rogen’s sizeable strengths, and considering that he’s surrounded by people like Paul Rudd, Jason Segel, and Leslie Mann (not to mention the scene-stealing Kristen Wiig, Bill Hader, and Craig Robinson), a director would have to actively try to make this one a failure. Luckily, it’s far from one, thanks in no small measure to Apatow’s keen sense of camaraderie.
7. Punch-Drunk Love (2002) (Director: Paul Thomas Anderson; Writer: Paul Thomas Anderson). Strange, colorful, and surprisingly, artfully shot and edited, this film is heartwarming in its fantastic simplicity. Adam Sandler is simultaneously endearing and unaffected.
8. Anchorman: The Legend of Ron Burgundy (2004) (Director: Adam McKay; Writer: Will Ferrell, Adam McKay). This one could be called a guilty pleasure, but I feel no guilt for liking something that has put me in stitches over and over again. Will Ferrell is at his showboating, dim-witted best. It’s undeniably, mind-numbingly silly, but that’s part of its charm.
9. Dumb & Dumber (1994) (Director: Peter Farrelly, Bobby Farrelly; Writer: Peter Farrelly, Bobby Farrelly, and Bennett Yellin). This is a perfect vehicle for Jim Carrey, and it allows him to do his best work in tandem with Jeff Daniels. These two performers showcase the pure magic of chemistry and the incalculable mileage to be gained from deplorably stupid lines delivered with naïve sincerity.
10. Groundhog Day (1993) (Director: Harold Ramis; Writer: Danny Rubin, Harold Ramis). I have to admit that this pick holds its roots in nostalgia; I watched it countless times as a child. Yet, if memory serves me well, this film gives Bill Murray plenty of opportunity to do what he does best. No one can play delectably bitter like he can.
Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)
Bullets Over Broadway (1994)
Office Space (1999)
Tommy Boy (1995)
The 40 Year Old Virgin (2005)
Step Brothers (2008)
Meet the Parents (2000)
Raising Arizona (1987)