Sheryl Crow "A Change Would Do You Good"

That moment when your husband calls out from the other room, "Honey, your old boss is here with a mattress." Let's back up a bit to explain. Imagine talking your way into a radio job with someone who really didn't want to hire you. If anything, he hired you because you wore him down. The two of you work together for a year or two and eventually he gets fired. You then assume your bosses old job and life carries on for both of you. A little while later, a sales person gets you an endorsement deal with one of the local bedding stores. The deal is simple: you record a bunch of commercials endorsing the bed and they'll pay you by giving you the bed you're endorsing. The client even arranged for a sleep expert to stop by your house and make sure the bed is to your liking. Guess who that sleep expert is? That's right -- your old boss. He's now standing in your bedroom with your husband to make sure your new bed is to your liking. Awkward? Yep.

Cyndi Lauper "I Drove All Night"

Roy Orbison originally recorded "I Drove All Night" in 1987, but the song didn't get released until 1992 (post-humously for Orbison).  Credit Cyndi Lauper for making the song a hit in 1989.  Several years later, Chrysler paid Celine Dion $14 million to endorse their cars.  As part of the ad campaign, Dion re-made "I Drove All Night" and turned it into a Top 10 hit on the Adult Contemporary Chart in 2003.