Always Leave Them Laughing (1949): As the cliche goes, comedy is a serious business, and who better to suck the fun out of the art than ... Milton Berle? For his first—and only—starring picture role, Uncle Miltie went semi-autobiographical, playing a vaudeville comic struggling to make it big while fending off accusations of plagiary. Berle himself was often accused of stealing jokes, but surely only being half-funny is more egregious, especially when the other half is a warmed-over melodrama in which our hero’s ego is repeatedly waxed by hot women like Ruth Roman.
Lenny (1974): Lenny Bruce’s daring and tragic life overshadowed his actual comedy even before this Great Man Biopic portrayed him as a martyr of free speech first and a pretty amusing fella a distant second. Dustin Hoffman’s cocktail party impersonation is nearly there, while director Bob Fosse, hot off Cabaret, nearly kills himself using self-conscious artiness to avoid the genre’s cliches, to little avail.
Punchline (1988): One of Tom Hanks’ early glimmers of deeper talent is present in this vaguely ‘70s-style drama about the desperation of the comic scene, with Hanks as an obsessive, self-destructive asshole and could-be star opposite, alas, Sally Field.
Bamboozled (2000): Spike Lee’s angriest and most savage film concerns comedy, natch. Damon Wayons’ self-hating TV exec pitches an openly racist show that hails back to the minstrel days, only for it to become a big hit. The bloody ending goes too far, but Lee made his point.
Nate & Margaret (2012): The difficulties of trying to do stand-up when you’re not that funny—or at least don’t yet have a voice—are realistically portrayed in this sweet indie, about the lived-in and unlikely friendship between a gay teen and a middle-aged frump played by Roseanne’s Natalie West.
Sleepwalk With Me (2012): If you, for some reason, long to see Ira Glass actually fuck up, imbibe his first screenwriting credit, in which he and cohort Mike Birbiglia find an underexplored area of stand-up—what does a comic do when s/he starts scoring laughs from bitching about his/her relationship without said paramour’s awareness?—then, soon as it’s established, unceremoniously drop it. Just like the other good ideas it has, annoyingly.