Tom Brady sat down with Caleb Pressley, formerly of Barstool, ahead of Sunday's Super Bowl for a segment that intentionally made the seven-time champion sweat.

The 32-year-old Pressley launched his weekly show, "Sundae Conversation," in 2021 and has since interviewed Drake, Aaron Rodgers , F loyd Mayweather , Jake Paul, Post Malone, Ed Sheeran, and others. He intentionally bates his guests into "gotcha scenarios."

Pressley previewed a new segment called "Color Commentator," referencing Brady's new gig at FOX ( where he inked a 10-year, $375 million contract ). “Amendola, Edelman, Gronkowski," he said while pointing at the seven-time Super Bowl winner. "What do you want me to say," a nervous Bready asked. "Color commentate," Pressley responded.

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"Patriots got a great lineup out there. When have guys like Gronk and Edelman and Amendola," Brady said before Pressley cut him off, shouting, "they're [all] white guys, Tom."

"In the Super Bowl this year, if you had to play against the Eagles, how many interceptions do you would mistakenly throw Cooper DeJean thinking he was one of your receivers," Pressley then asked the FOX commentator, generating a massive chuckle.

The 22-year-old DeJean intercepted Kansas City Chiefs quarterback Patrick Mahomes midway through the second quarter to give the Philadelphia Eagles a 17-0 lead.

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This wasn't the only notable moment on 'Sundae Conversation.' Pressley later asked his co-host Glenny Balls if he ever owned any Bitcoin, and he answered "yes" before admitting he lost it in a company that went bankrupt. Brady lost nearly $30 million when crypto company FTX went under in 2023.

Brady survived the first half of Super Bowl LIX without any broadcasting hiccups. He immediately jumped to FOX's top commentating team in his first year, supplanting incumbent Greg Olsen.

Olsen made a cryptic comment in early February indicating he was gripped for the part, but he recently cleared up any misconceptions over his feelings.

"I want to be very clear, you know. And I know my comments last week kind of took on a crazy storm. I actually talked to Tom, I've talked to Tom regularly throughout the season," the former NFL tight end said.

"We've gotten to know each other really well, I have a ton of respect for him which goes without saying as a player."

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