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Staff & contributors
Too Funny to Fail isn’t just a documentary about funny people. It’s a documentary that’s hilarious in its own right. Director Josh Greenbaum assembles the comedic powerhouse behind the short-lived Dana Carvey Show and has them recall the idiosyncratic, subversive skits they did on the show. They are, of course, naturally funny, but it’s the questions Greenbaum asks them off-cam, the clips he shows, and the titles he picks for them (Bill Hader, as a fan who used to watch the show in lieu of going to classes, is stuck with “once skipped school”) that gives the documentary its own comedic signature. The spectacular failure of The Dana Carvey Show is also an inspirational story of sorts, given the astronomical success its staff and cast have and are continuing to enjoy since its cancellation.

Genre: Comedy, Documentary

Actor: Bill Hader, Dana Carvey, Jon Glaser, Louis C.K., Robert Carlock, Robert Smigel, Spike Feresten, Stephen Colbert, Steve Carell

Director: Josh Greenbaum

Rating: NR

, 2023

Those who grew up watching baseball legend Reggie Jackson will know that his was a name you read all over the news. One of America’s first athlete superstars, Jackson had a reputation that preceded him—he was a celebrity you’d just as soon find in Studio 54 than in the gym, wearing diamond bracelets more than baseball mittens. But in his self-titled documentary Reggie, he finally tells his story in his own words. 

Reggie tracks his career in the context of the constant racism he and his fellow Black players in the league faced for many years. He explains why building the tough persona the media condemned him for years was necessary. It’s as autobiographical as it is historical, with Jackson often discussing how race informed every part of the sport, whether he wanted it to or not. The documentary is fascinating and informative, and it serves as an essential reminder of the inequality and double standards POC players faced and continue to face today.

Genre: Documentary

Actor: Hank Aaron, Julius Erving, Reggie Jackson

Director: Alex Stapleton

Rating: PG-13