17. The Match
In 2020, Tom Brady participated in ‘The Match’ against Peyton Manning. The golf showpiece saw the legendary quarterbacks team up with Tiger Woods and Phil Mickelson. In the end, Manning’s team saw victory but it was an entertaining show for TV viewers to watch.
However, Brady endured an embarrassing wardrobe malfunction as the cameras rolled. He bent down to retrieve his ball but then his pants ripped. Luckily he wore underwear because it would have been even more of a disaster. It wasn’t the finest moment of his iconic career (via Golf Digest).