The number of people trying to become famous comedians in New York City may be vast, but the world of working professionals is tiny—a much-envied tier of perhaps 50 regulars, all on the cusp of fame, who get the prime slots in the city’s best comedy clubs.

It is these comedians, not the big names of the national touring circuit, who receive the most respect from their fellow performers. Success on the road is seen as a matter of getting laughs from the unsophisticated audiences of small city clubs and college amphitheaters. Killing in New York means winning over those other comedians looming in the back of the room.

And that’s what Greg Giraldo did for the last 17 years. Giraldo, who died of an accidental drug overdose on Wednesday, was one of the two or three best club comedians in a roster that has included Chris Rock, Dave Attell, and Colin Quinn. He was smart, he was tough, he was original. The phrase “comic’s comic” gets tossed around, but Giraldo was the real deal.

“Even within in the NBA, there is a subset of players that is head and shoulders above the rest,” Noam Dworman, a friend of Giraldo’s and the owner the Comedy Cellar, told me. “And Giraldo was one the few comedians who was totally in a different league, even among the best.” ( Read some of the celebrity tweets on Giraldo’s death here).

He was a Harvard Law grad who was streetwise enough to demolish a heckler. There’s not much video of him tangling with a audience member, but you get a sense of how quick he was in this exchange with a humbled Denis Leary:

Giraldo Defeats Dennis Leary (fireworks begin at 3 minutes 20 seconds)

It seemed odd to those who’d seen him live that Giraldo made his reputation on television as a hired gun on Comedy Central’s roasts. There was no disputing that he was good at it, but to use Dworman’s analogy, it was a bit like watching Michael Jordan in a free throw contest. Sure, he’d make 19 out of 20—and Giraldo was always the best on those shows, despite neither the audience nor the roastee knowing who the hell he was—but what about all his other moves?

You could sense that Giraldo himself wasn’t quite sure what to make of his feats as a roaster. After his 2007 evisceration of Flavor Flav, he may have taken some heat for making racial jokes. Not long after, he started being introduced as “Latino comedian Greg Giraldo,” I imagine to give himself the leeway to make fun of Latinos (and everyone else). But four minutes of roasting isn’t starring in a sitcom or headlining Carnegie Hall, and I’m happy he’ll never see that in his obituary on The Wrap, the author wrote that he was “Considered a fast-talking ‘insult comic.’”

The Comedy Central Roast of Flavor FlavUncensored - Greg Giraldowww.comedycentral.com South ParkNick Swardson's Pretend TimeUgly Americans New Episodes

Giraldo was a part of a number of TV projects, but whatever traits mass media success requires of a comedian, either Giraldo lacked them or producers never knew what to do with his talent. I wrote a few months ago how nice it was to see him as a judge on the most recent season of Last Comic Standing and hoped this would finally be the breakthrough he deserved.

We’ll never know.

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Gregory Gilderman is a senior editor at The Daily Beast and a former writer for Philadelphia magazine. In 2007 he was a finalist for the Livingston Award, a prize that recognizes journalists under 35.