1. Carrie Fisher
Carrie Fisher, the author of Wishful Drinking, and Chelsea Handler, the author of Are You There, Vodka? It's Me, Chelsea, are kindred spirits. Carrie Fisher's prose may be more decidedly "bipolar" (her words, not mine), but I'd love to see the two engage in a sincere discussion about tequila preferences and Paul Simon's genitalia.
2. Elizabeth Taylor
Our greatest living movie star has proven with Larry King and on Twitter that she'll open up at will. Chelsea's provocative curiosity could be the key the getting Taylor to gab about Monty Clift's private life, Larry Fortensky's haircut, and whether Who's Afraid of Virginia Woolf ever feels like real life to her.
3. Sarah Palin
Dream scenario: Sarah Palin starts talking about her TLC series, Chelsea demurely asks how many times a day she calls herself a "mama bear," Sarah politely chuckles, and Chelsea responds, "Because your daughter has expressed interest in becoming a gorilla" before showing her this footage and setting it to circus music.
4. Joan Rivers
How haven't these two crossed paths yet? Though Chelsea may have mocked Joan's plastic surgery in an interview with Katie Couric, the two could spend hours reciting Kardashian one-liners at each other.
5. Tina Fey
Tina Fey's best interview to date was on The Howard Stern Show when she opened up about terrible SNL host Paris Hilton. If there was ever a female heir to Stern's mode of badinage, Chelsea's your girl. The pair might converse openly about Alec Baldwin, Tracy Morgan, and whether Lorne Michaels is kind of a creep.