The pair, however, still have their work cut out for them, as evidenced by Damon's attempt to sneak onto the show disguised as Kimmel's actual guest, Dr. Phil. Sporting a horrifying bald cap and mustache, and spouting faux Texas-isms — "A squirrel in a top hat is like a donkey in a dress: You can take it to the prom, but if you try to make it wear lipstick, you're gonna get kicked" — Damon did finally take a long-coveted seat in the guest chair, but Kimmel blew his cover.
While Damon believed Kimmel had finally acquiesced to letting him on the show during therapy, the host insisted he had only said he would "try" to squeeze the actor in.
Kimmel and Damon's feud dates back to the early days of Live! when the host wasn't yet welcoming top tier guests and would end his show by joking, "Apologies to Matt Damon, we ran out of time tonight." As the show's popularity grew, Damon started popping up, but Kimmel regularly found a reason to bump him. Their spat took off in 2009, however, when Kimmel's then-girlfriend, Sarah Silverman, debuted her confessional smash single, "I'm Fucking Matt Damon." (Boston.com has compiled a helpful timeline.)
As detailed during the session, Damon has been waiting to appear on Jimmy Kimmel Live! for 12 years, and since he's technically scheduled each night, he has to show up. While Kimmel defended the prolonged delay by noting his one-hour show has other guests, a band, a monologue and "important commercials," the pair quickly started sniping at each other.
"He is verbally abusive to me and couches it as 'truth.' What am I supposed to do?" Damon asked.
"When you wanted to buy that zoo, what did I tell you?" Kimmel replied.
"That zoo was for both of us! That zoo was supposed to be something beautiful!"
As the session continued, Damon revealed that he doesn't just show up each night, but actually lives in the dressing room, while Kimmel insisted that the actor was a spoiled star who could not accept that Kimmel wasn't his show.
"It was that one time," Damon replied. "I took the shit over and fucking busted the ratings wide open."
"You taped up my head!" Kimmel said of the experience. "It felt like duct tape was suffocating me."
Still, the pair inched closer to a breakthrough, with Kimmel admitting he liked some of Damon's friends, and Damon saying, "I like his show — I wouldn't have waited for 12 years to get on if I didn't like the show." In closing, Kimmel promised to get Damon a small TV (but no Wi-Fi) for his basement dressing room apartment, and try harder to actually have him on the show. Though the host quickly qualified, "Just not tonight because this counseling thing has gone on a long time."
After the clip of the session ended with an emotional — and destructive — hug, Kimmel remained true to his word, ordering Guillermo and his security detail to escort Damon off the set.