Commercial: AT&T (2009)

The youngest Wilson brother gained tons of fanfare for starring in huge comedies like Old School and The Royal Tenenbaums. Then his career hit a roadblock after the 2007 bomb My Super Ex-Girlfriend underwhelmed at the summer box office. Soon after, he jumped at the opportunity to star in AT&T’s 3G commercials, which poked fun at the network’s mobile competitors (mainly Verizon). An insider claimed Wilson was miserable during the shoots because he was frustrated about doing commercials to make a living as an actor. Go figure.