Robin Hood: Men in Tights (1993)

The friendliest late Brooks film, and a good pick for watching with teenagers. Its plot is loosely built on Kevin Costner's Robin Hood: Prince of Thieves (1991), so a vague memory of that film is all the prep you need, though Errol Flynn fans will catch the jokes aimed at his 1938 version too. Cary Elwes plays Robin with a straight face that sells the silliness, and Dave Chappelle makes his film debut. Critics were mixed in 1993 and it has since built a cult following. The humor is broad and pun-heavy rather than sharp, which is why it ranks below the 1970s films, but between the Sherwood Forest rap and the singing Merry Men it is pure fun.