23. "Let's Duet"
Movie: Walk Hard: The Dewey Cox Story (2007)
Though it's not exactly uproarious, director Jake Kasdan's 2007 send-up of conventional biopics, Walk Hard: The Dewey Cox Story (co-written with Judd Apatow), has its fair share of memorable jokes and visual gags, chief of which is the pun-filled song "Let's Duet."
Crooned in collaboration by Dewey Cox (John C. Reilly) and Darlene Madison (Jenna Fischer in person, Angela Correa on vocals), it's a ridiculous track that's made funny due to how straightforward it's delivered by all involved. Dewey sings, "In my dreams, you're blowing me…some kisses." Later, Darlene belts out, "You can always come in my backdoor." Romance, by way of Apatowian perversion.