It makes sense, I suppose, when one is at the pinnacle of their career in one field to dream of conquering other worlds. Jordan tried to play baseball, 50 Cent sells water, etc. This is why, as you ascend to professional heights, it’s good to surround yourself with smart advisers rather than yes men. Unlikely the folks on the following list, you’ll then have someone to tell you not to cut a record.

Paris Hilton

In her defense, Hilton wasn’t actually trying to transition from mastery in some other field. Had her musical aspirations succeeded, that would have been the first thing she was good at. Well, maybe not…

Leonard Nimoy

As the infamous “The Ballad of Bilbo Baggins” was recorded in the sixties, I like to believe that hallucinogenic were somehow involved. What other excuse could their be?

Bill Cosby

Given his legendary abilities as comedian, it is entirely possible that Cosby recorded the hilarious songs on Disco Bill as an elaborate joke. But with his history of rape allegations rising to the public consciousness, the thinly-veiled lewdness of the come-on chorus “What you think about lickin’ my chicken?” takes on a whole new creepiness.

Jada Pinkett-Smith

From acting to music: Someone close to her should have warned Pinkett-Smith about the difficulties of trying to pull off what has probably come to be known in her house as a “Reverse Will.”

David Hasselhoff

Keep in mind that labeling the original Knight Rider’s music career ill-advised is an entirely esthetic appraisal as I’ve heard it has also been quite, miraculously lucrative.