The 40-year-old comedian sat down with host Kimmel to discuss his new film, Uncle Drew -- where he plays the self-identified "token white guy" in the comedy, which also stars NBA players Kyrie Irving, Nate Robinson, Reggie Miller, Chris Webber and Shaquille O’Neal. While recounting getting the chance to play hoops with Irving, Kroll's pants split right down the middle.
"I got to play basketball against him. You don't think I'd hold up well against Kyrie?" he asked the laughing crowd. "I was literally like, 'I know I'm not in the NBA, but, you know, I was pretty good on my Jewish day school team.' I was like, 'I'm going to hold my own.'"
Kroll then recalled playing some decent defense and even scoring a layup on Irving, but his cockiness didn't last long — neither in the story he was telling nor on the stage with Kimmel.
"So now I'm cocky, I'm going back on defense and I'm like, 'I got Kyrie. I got Kyrie.' I'm hitting the ground and then," Kroll started, bending over to act out a motion before suddenly announcing, "I just fully split my pants!"
The giggling crowd and Kimmel both had a laugh at Kroll's expense, while the comedian turned it into a joke of its own.
"Wouldn't it have been amazing if there was a full-on poop stain?" he quipped. "So, basically I did the physical equivalent of splitting my pants playing defense against Kyrie."
Kroll continued his self-deprecating humor following the show on Instagram.
"And thanks to my stylist @jeanneyangstyle not only for the pants that split but for sending me these beautiful pics taken right after they split on #jimmykimmel," Kroll wrote alongside photo collage of his split pants.
ET recently caught up with Kroll and he gushed about working with the NBA legends in Uncle Drew, hitting theaters on June 28.
"It just was one of those jobs where I was like, 'This is all I could ever ask for,'" he said. "I feel very lucky in general have the jobs I get to do. But this one in particular felt like what a fun combination of things."
Kroll also talked about watching Irving transform into an older version of himself for the movie.
"I have a picture of Kyrie -- were in the parking lot. We're all in our little trailers getting ready to go to set and so he's got the makeup on," he recalled. "He hadn't got into his wardrobe and, like, his belly. So, you've got Kyrie, like, ripped, like, 25-year-old Kyrie with, like, Uncle Drew face -- and you're like, 'What is going on here?'"
Here's more with the funnyman: