Let's list good bands and musicians who tried something cringeworthily different.

Cafe Society
21

Captain Beefheart’s attempts to make normal mid-70s music – Unconditionally Guaranteed and its follow-up Bluejeans & Moonbeams – seem pretty much universally loathed by his fans and met with utter indifference by everyone else.

Violent Femmes frontman Gordon Gano released a gospel album under the name Mercy Seat. Eek. Why can’t he get just one fornication?

I think the Chris Gaines thing best suits the concept of “cringeworthy,” though. I’m thinking of the heavily Photoshopped pictures of Mr. Gaines in particular. Gah!

22

David Lee Roth did a Van Halen cover album in the style of bluegrass

23

I can never decide if that was a parody or not. Either way, it was beyond “cringeworthy”.
I nominate John Fogerty’s “Centerfield.” This, from the guy who gave us “Proud Mary”, “Born on the Bayou”, “Fortunate Son?”

And let’s not forget KISS deciding to do the power ballad, “Forever”, sans make-up. shudder