Sandra Bullock was discussing her nude movie scene when David Letterman jumped in with jokes about modesty pads, turning the moment hilariously awkward. The video then cuts to several classic celebrity roasts: John Cleese and Eric Idle teasing each other about marriage, Martha Stewart growing suspicious of Letterman’s obsession with her jail experience, and Don Rickles mocking Jay Leno’s famously large chin. Charlize Theron playfully shut down Letterman’s curiosity about her Vogue photoshoot, while another guest joked about pregnancy giving her “a rack and a half,” sending Letterman struggling to maintain eye contact. Joan Rivers delivered her trademark no-filter jokes about Angelina Jolie and even said she hoped her grandson would grow up to be gay so someone would care that she knew Judy Garland. The montage ends with Raquel Welch and Letterman flirting as she demonstrates a pose, joking that viewers won’t get to see it “from that angle.”