23. Woody Allen and Mira Sorvino in Mighty Aphrodite (1995)
Why wouldn't director Woody Allen want to star in his 1995 romantic comedy Mighty Aphrodite? Even though the legendary filmmaker resembles Mr. Smithers with a more proportioned head and reading glasses, the proud New Yorker gets to cavort with beautiful actresses like an in-her-prime Mira Sorvino. Now that's business and pleasure!
Still, it's impossible not to cringe whenever Sorvino's character, hooker/porn star Linda Ash, gets frisky with Allen's expectedly neurotic Lenny Weinrib. By imagining what Sorvino would be like in bed, the same thoughts attach themselves to Allen, and that's not something you want to creep into dreams, whether during the day or at night.