When did that happen? I can't find that in the manga.
That clip was from the first Broly movie.
That said, I'm gonna change my answer a little bit...
Krillin had the
most L's besides Yamcha, but Vegeta and Gohan took the
bigger L's.
Krillin got the brakes beat off of him but he still got 18, and still became the strongest human ever (except for arguably Tien), so he still won in the end considering he was just a regular, humble dude who KNEW he wasn't seeing Piccolo or the Saiyans.
Vegeta's losses and deaths weren't as frequent but were way more humiliating than anything that happened to Krillin IMO just because of his pride and arrogance. He brought so much of it onto himself. Dude spent his whole life working as a lapdog for Frieza, tried to fight him on Namek thinking he was a Super Saiyan, got bodied, and died crying like a punk. Then he became an actual Super Saiyan, started feeling himself, and then got his arm broken by a woman who eventually let Krillin (of all people) smash. Later on he sold his soul to try and get his chance to show up Goku, a decision that not only got him killed, but also led to the destruction of the entire planet.
I think Gohan had it the worst. He got
after he grew up.
He went from being THAT DUDE and the GOAT protector of Earth against Perfect Cell... and turned into a lame running around in a cornball superhero outfit striking suspect poses and getting embarrassed by villains he could have beaten as a 6th grader. Krillin was relatively weak, but at least he came up from where he started. Gohan's whole life peaked in middle school
I'm crying.
on 
