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

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.

"Yeah like that big russian war." Underrated part of the clip

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

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

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

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.

When Greg says "Maybe there's a nonviolent way to solve the problem" he's CLEARLY setting up a bit. But then oblivious Leary interrupts like it's a serious political discussion! As a comic he should have see that and not stepped on the joke.

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.

"That big Russian War." I will remember that forever. It is so sad that Greg had to leave and stick us with Denis Leary. Greg was one of the best comedians ever. Leary is just a hack.

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

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

Dennis Leary hasn't been funny since Bill Hicks died.

“Oh yeah that big Russian war” Took the crowd a second LOL

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

Greg uses intelligence, it's super effective.

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

"yea like russia, that big russian war" dude, the shit was over before it began. l

That "that's kind of what we do here Denis, as a comedy writer" was frigging gold! Everything about it: the way he just sat there calmly, with the line in his mind, waiting for Leary to stfu with his babbling, delivered it calmly with perfect timing.

It's always a hoot when a "tough guy" like Leary tries to bully someone and just gets blasted. Giraldo totally rocked him back on his heels.

The wrong one died.

We miss you Greg. You and Patrice are entertaining another fan base in a far away dimension but your legend lives on.

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

Greg Giraldo is a legend

When Denis Leary said, "You're the guy in school that did all the homework and then asked if there was any more that needed to be done," Geraldo should have replied by saying, "and you're the kid who never did his own homework, you just copied Bill Hicks'"

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

"You started it and I finished it"? No Dennis, you no talent hack: You started it and Greg finished you.

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

I always liked how Denis said, “you started it, I’ll finish it.” No. You started it. He finished it. He bodied that Bill Hicks wannabe. That’s why Giraldo is a legend and Leary is just a self-involved sellout.

"You come at the king, you best not miss"

The irony is that Greg's response was improvised. There's no way he could've written that before the show and even if he had, that's his job (like he said).

When giraldo said the Russian war comment Leary looked legit stunned haha

Leary got owned. Wow

Dennis bit off way more than he could chew against of the most clever comedians that has ever graced comedy. I'm thinking the last thing anyone would ever want to do against the late, great, Greg Giraldo was have a battle of wits with him.

You go against an Ex-lawyer, what do you expect.

I love the look on Giraldo's face...he had that comeback ready. You could see he was just waiting for the quiet before he induced the storm! lol Love that guy, and the comedy world misses him badly. I don't think the comedy world even noticed when Leary was gone from it.

this wasn't enough versus. Colin Quinn should have put his knee back down and let Geraldo finish off Leary

Damn, that almost got ugly. Good thing Colin Quinn put his leg on the table.

I'm surprised Leary didn't steal Giraldo's jokes when he past away

The way Colin puts his leg up on the table was a subtle way to defuse the situation.

Greg Giraldo was the best "no name" in comedy. You can tell a genuine talent by the fact that all his peers loved him.

That's what we do here Denis... a little comedy writing.

I love how Dennis says "let's go in" the guy has never been in the army or done any form of public service and says "let's go in" like war is no biggie

"Do u know how short u have to be to have napoleon's complex in north Korea?", that's why he was of the greats

Rest in peace Greg, the REAL Roast-master general.

3:27-4:28 is the best part of this clip. I watched this show often when it aired in 2002-2004. I miss Greg. He deserved more recognition and success than he received. Respect to you, Mr. Greg Giraldo. You left this earth way too soon in 2010.

Too bad that Bill Hicks wasn't there to help Denis to make a comeback.

This was awesome! Greg was an assassin.. Dennis was livid to say the least!

WTF...Why did stardom bypass Giraldo but reward Leary, Dane Cook, Larry the Cable Guy, Jeff Dunham, etc...????

Maybe Leary will get some more work if another Ice Age comes out.

Dennis should have just took that first loss. He got but hurt about it, and then dug himself into a deeper hole

Giraldo owned him. No two ways about it.

Dude was trying to act like the coolest guy in the room so fucking hard. Glad Greg got him rattled.

Damn... Leary got stomped *hard*... and he had nothing... just a pissy little "did you ever have a show?" What a failure of a comedian. It's no wonder he bailed on stand up comedy as soon as he got big.

Giraldo was trying to set up his Korean nail salon joke and Leary f'd it up by getting all serious. The "Big Russian War " was a brilliant & witty comeback.

That big Russian war. Leary OWNED!! Absolutely priceless

I forget who it was, but one of the cellar comics summed up this entire ordeal perfectly. Greg didn't even have to use the the nuclear stuff - the joke thievery. He was smart enough to riff circles around Leary.

The thing that really bugs me about this is that Greg was setting up a joke. Leary shit on his set up. Like what kinda comedian does that? Obviously there is a joke coming it's FUCKING COMEDY CENTRAL!

Wow, he's so cool. He's wearing shades indoors. What a cool clever guy.

Doesn’t surprise me watching this that Giraldo went to Harvard and was a lawyer

"that big russian war" hahahahahahh leary always makes an ass out of himself

Greg was an awesome comedian he was hilarious. His memory lives on with his comedy and videos of him roasting others, his stand ups he was great

Denis Leary deserved this every time he stepped in the spotlight. The man ripped off America's GREATEST Comedian, who unfortunately was censored and ultimately passed away from Cancer. Bill Hicks was the best...and always will be.

I'll never forget this. Thank you for posting this. Everyone was great, Lenny Clarke is great and r.i.p Greg Geraldo.

One of the greatest comedians of his generation. Roast in peace Greg, you are missed.

What's interesting about this is that Greg's "written" jokes that got the biggest laughs on the show, didn't get as big of a laugh as his improvised jokes! He didn't actually need to write anything. He could've just showed up one minute earlier and still be the funniest person on the show. RIP

At a Last Comic Standing audition, Greg Giraldo told me that I had potential. He will always be one of my comedy heroes.

After that Russian remark... Denis Leary's next special... Denis Leary: yeah remember that big Russian war we had with Russia.

Greg was so fast, he had a response ready as soon as Dennis closed his mouth Feel like Dennis still thinks about this every day 😂

I just noticed how Colin put his leg up in between them on table, not that a leg would stop them in reality, but as a signal that the didn't want it to escalate anymore. What a great show.

I watched this live and was a huge Denis Leary fan at the time. Denis was a GIANT and it felt like he was giving to charity by appearing on a Comedy Central show that came on at 11:30. Not to sound condescending, but it was kind of a big deal that he was on Colin's little show. (BTW, I loved Tough Crowd and CQ), and this was appointment television. What happened next was a comedy disemboweling we have never seen since. When it was clear Denis came in to perform off-the-cuff and was willing to survive off wit alone (which I did think he had clever moments), Greg went in for the kill. Leary was no match for a smarter and more prepped Giraldo. Greg allowed Denis to stumble over his own feet and executed him standing. This is brutal, and hilarious, to watch.

At 3:38, Leary has this look on his face like "how did Greg flip this around on me." His expressions every time Greg says something funny are priceless.

4:20 one of the best lines ever in live tv...maybe the best.

Here from the Hey Babe Pod 👏🏼😂

Leary admitted on his own later on, that Giraldo got the better of him here.

It never gets old watching Greg putting Leary in his place

Giraldo was justifiably merciless in vanquishing one of comedy's most prolific hacks.

I remember seeing this live and thinking: that's a classic moment in comedy TV history and it's gone forever, now here I am watching it again

That Russia comment really pissed Leary off . Thought for sure Giraldo was gonna call Leary a joke theif when he went after his joke writing

4:08 body slam for Giraldo. Miss that guy.

I feel that too many have forgotten Greg. Fantastic comedian

I just love how Giraldo is IMMEDIATELY ready to fire back whenever Leary makes a comment- dude has the look in his eyes of a prizefighter who knows he's about to land a knockout.

Leary was, is, and always will be one of the biggest comedic hacks in history.

You play with the bull, you get the horn.

The late great Greg Giraldo! Quick on his feat, funny AND making valid points. RIP

I saw his the entire vide of all the roasts he was ever in. Without a doubt, you could tell how smart and brilliant he truly was. Not to mention he was a lawyer. He was incredible in every sense of the word. He is and always will be missed 🙏🙏

When you resort to the , "Yeah my show, did you ever have a show?" insult. You know you got your shit handed to you. 🤣

greg is and always will be the dude. so quick to come back at leary in this segment and pretty much embarrassing for dennis

I can now see how being a trained lawyer and an experienced comedian would be great attributes for either profession.

RIP Giralddo. You made me laugh.

Sad Greg is gone. He was a Legend. My favorite. I was too young to ever see him live. But still listened over the radio. Good times.

IMO There was nobody better at insults than Giraldo

Denis Leary is a man of many talents, and those talents include: plagiarism, theft, pretending to have talent, pretending to be a comic, and pretending to be a tough Boston gangster. Did I mention plagiarism and theft? "You know what...you're the guy in school that did all the homework and then asked if there was anymore that needed to be done." Yeah, good one Denis...that was real clever. Those stupid kids turning in their homework and then doing extra work too, they're so stupid. We wouldn't want kids doing their homework and then looking for more to do - the kids might actually acquire knowledge and learn a thing or two about taking initiative. We wouldn't want those kids learning to apply themselves or learning to rely on themselves or learning to work hard for something. I'm guessing that Greg Giraldo was the guy in school that did do all of HIS OWN homework and turned it in, while Denis Leary was the guy in school that copied Greg Giraldo's homework and then bragged as if it were is own work when he got an A. Denis was also probably that kid in school that just had to be heard - that kid that just always had to speak over somebody because he thought that he was so profound and suave and cool and original, but all that really came out of his mouth was drivel. The only thing more fake than Leary's standup is his Boston-tough-guy act. You don't fool me Denis.

This was so incredibly satisfying! I loved Leary in his prime. I was the right age for it. You could tell Giraldo wasn't happy about having to engage like that, and it makes him even more legendary. He had no choice really. But he damn sure stood up to Dennis in a big, big way.

Irony. Leary pointing out that someone writes jokes. He's used to just taking other people's work. Hack!!

LOVE, LOVE, how Greg puts that little thief Leary in his place it was beautiful!!!!! We miss you Greg.

Greg had all that prepared. It may have seemed like he improvised, but he was legendary for his writing from every possible angle. He did his homework and came in ready for anything and that is not an easy task. It kind of lessens what he was capable of doing to think that he didn't put a lot of work into being so funny.

I like how Colin got in between them at the end of the clip.

No comic could go toe to toe with Greg without regretting it afterwards. The True Roast Master General is Greg Giraldo, May he Rest In Peace !