Greg Giraldo would've been perfect in this podcast era. He was smart, articulate, clever and thoughtful.

Leary could have avoided looking like a prick if he were only able to laugh at himself.

This segment is what turned Greg Giraldo from a great comedian and roaster to a legend.
He dismantled Dennis Leary.

The irony of joke thief trying to put down someone for writing jokes.

"Yeah like that big russian war."

Underrated part of the clip

Giraldo: "If you actually wrote your jokes, maybe your show would still be on the air.

FATALITY!!

Oh man. I remember being in high school and watching this in the darkened living room of my childhood home when it first aired. It was the moment Greg Giraldo, for me, transformed from a comedian I really liked to a kind of a personal hero- standing up to the loud mouthed bully who talks shit, but can't back it up. Giraldo's death was one of the very few celebrity deaths that personally affected me and I just want to say RIP Greg. We miss you.

The best thing about this is giraldo was just setting up a joke but when Leary challenged him he went nuclear.

Greg Giraldo is a legend

Giraldo was the quickest wit in the game. By far the most under underappreciated comedian in years. He was the only reason I watched the roast on comedy central.

"This guy writes so many jokes before the show." "Yeah denis thats what we do, I'm a comedy writer." That's comedy gold!

Leary got so flustered he actually said “this guy writes so many jokes before the show it’s not even funny” like it was an insult. He’s such a d bag he forgot what a comedian is

if Jeff Ross is the roast master general then Greg Giraldo is the roast master God.

“Oh yeah that big Russian war”

Took the crowd a second LOL

Everyone with a brain misses Giraldo, nobody with a brain misses Leary.

Giraldo completely shut him down with the "Russian war?" comeback. Brilliant

Greg uses intelligence, it's super effective.

Leary got owned. Wow

One thing we have to acknowledge; Dennis commented on this moment in the documentary honoring Greg. He flat out said that he "looked like a real asshole" in that moment and was very complimentary towards Giraldo. Gotta give the guy props for owning it after the fact and eating some humble pie.

Greg was a damn genius. Academically and comedically. He was in the top 1 percent of his Harvard law school.