The 5 most awkward moments from Netflix's Tom Brady roast: Kim Kardashian booed, Gronk's glass smash

Jeff Ross gets told off, Kim Kardashian gets booed, and more.

There's always a risk when you bring in a non-comedian for a roast. Comedians have to develop a thick skin in order to survive hecklers and haters, but star athletes are more accustomed to being cheered on and worshipped. So when a legendary NFL quarterback sat down for Netflix's The Roast of Tom Brady, there were definitely some awkward moments amidst all the jokes.

A shot glass is not a ball: In the final decade of his time leading the New England Patriots, Brady had no better partner than Rob Gronkowski. So naturally, the retired tight end was in attendance at Brady's roast. But when the two took shots together, it seemed like Gronkowski may have forgotten he wasn't on a football field anymore, and spiked the shot glass after he finished. Unlike a ball, those things are made out of glass, and could potentially hurt someone.

"Don't say that s--- again": Even outside the NFL, Brady is still protective of his old boss. When roast master Jeff Ross took the stage, he had not just Brady but also Patriots owner Robert Kraft in his sights. Reenacting the first conversation the two had, when 199th draft pick Brady confidently told Kraft "I'm the best decision your organization has ever made,” Ross added, "Would you like a massage?" The dig at Kraft's 2019 arrest for soliciting prostitution in a Florida massage parlor clearly made Brady uncomfortable enough to take the stage and whisper "don't say that s--- again" in Ross' ear. The expert roaster was rattled by that experience, made even worse by host Kevin Hart's subsequent dismissal: "Make sure to check out Jeff’s one-man show. It’s playing at the Hollywood Cemetery. His career is literally dying. If we stop doing these roasts, you will not see Jeff Ross ever again.”

Ghosts of girlfriends past: Before he married supermodel Gisele Bündchen, Brady was in a relationship with actress Bridget Moynahan — and the timing of their breakup came up for ridicule during the roast. “Tom, you’re the best to ever play for too long, you retired then came back then retired," comedian Nikki Glaser joked. "I get it, it’s hard to walk away from something that isn’t your pregnant girlfriend.” Brady reportedly left Moynahan for Bündchen before he knew of the pregnancy, which Glaser also joked about: “To be fair, he didn’t know. He just thought she was getting fat.”

Kim Kardashian can take it: When Kim Kardashian took the stage to join in the roasting, the audience initially greeted her with some cheers, but those were quickly drowned out by a massive wave of boos — so much so that the reality TV star couldn't even get through her first joke and needed Hart's help to calm down the crowd.

Don't mention the dad: Those boos weren't the end of Kardashian's grief, though. When Brady had his chance to fire back, he targeted her ex: “I know Kim was terrified to be here tonight. Not because of this but because her kids are home with their dad.” Even after a week with a high-profile hip-hop feud between Drake and Kendrick Lamar, Kanye West's recent antics still make him the most controversial rapper around.

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