The late-night talk show host showed up in a blouse, clogs and a wig for his guest appearance on "The View's" live broadcast from Walt Disney World in Anaheim, Calif., People.com reported.
"Who are you supposed to be?" panelist Joy Behar wondered aloud.
"I think you know who I'm supposed to be," Kimmel said. "Things ended abruptly with Rosie and I wanted to give you ladies a chance to say goodbye."
"View" panelist Sherri Shepherd also grilled Kimmel about his recent second split from his longtime girlfriend, Sarah Silverman.
"The only thing better than breaking up is going on 'The View' right after you break up," Kimmel said. "It's really (like) living a dream."
Pressed to reveal what went wrong with his relationship, Kimmel quipped: "What do you mean, what happened? Look at me. What do you think happened? I'm a 41-year-old man with a bra filled with Koosh balls. I'm an imbecile. She couldn't date an imbecile anymore."
So does that mean there's no chance of another reconciliation?
"I don't know, ask her," People.com said he replied.
Celebrity Breakups and divorces of 2014 [PHOTOS]