Dodgeball: A True Underdog Story (2004)

Song: "Apache"
Artist: Sugarhill Gang

To save their gym from corporate overhaul, a motley crew of dodgeball players must defeat Globo-Gym owner White Goodman (Ben Stiller), who'll shut them down if he wins the game. However, in an attempt to woo former employee Kate Veatch (Christine Taylor), Goodman busts out the big guns. Showing up to impress her in a stark, crisp ensemble, he walks up as "Apache (Jump On It)" plays, and you can't help but wonder if that's what his white shoes make him want to do.