endorsing a Chrysler... not such a good idea, but they paid Frank Sinatra enough, and he did it, and then regretted it

Sinatra appeared in print ads and television commercials in which he sang a specially penned song about the luxurious car called “It’s Time” … for Imperial.  That special edition included badging and a Mark Cross leather case with 16 cassette tapes of Sinatra songs.

 Chrysler Chairman Lee Iacocca, gave one to Frank in gratitude for Sinatra’s agreeing to promote the car without charge while the automaker was struggling to avoid bankruptcy.

It stalled on Sintra in the middle of a busy intersection and Frank walked away from it, too embarrassed to be seen with it.
http://www.hourdetroit.com/Hour-Detroit/January-2012/Frank-Sinatra-in-a-Chrysler-Imperial-1980/#.U6h-kPldVTM
and http://www.imperialclub.com/Yr/1981/1981FS/index.htm