Caitlyn Jenner created a super awkward moment when she asked John Leguizamo if he enjoyed dressing up like a woman.

Caitlyn was a guest on 'Live' with Kelly Ripa, and John was her guest co-host. CJ made a callback to John's classic role in "Too Wong Foo, Thanks for Everything! Julie Newmar" ... where he played a drag queen.

He was brutally honest about the experience. Kelly seemed to squirm. Caitlyn's reaction -- you should see what I've gone through!

Pretty sure it's not a competition, but Caitlyn's right about one thing: John did slay in 'Wong Foo' ...