Giraldo excelled on Tough Crowd: he was a frequent guest and a crowd favorite. “He was the best. I mean, he just was never flustered. He was committed.” [Judy Gold] The format suited not only his intelligence and his quick wit, but also the habit he had throughout his career of always writing and always being prepared.

Giraldo did his homework. Many of the other comedians who appeared on Tough Crowd cite Giraldo’s prodigious preparation. Rick Dorfman says that “Greg didn’t dick around in his show prep for Tough Crowd. He adopted a studious, workman-like approach to topical joke writing.” Judy Gold says that Giraldo inspired her to “over-prepare” because “he did work so hard and he was so well-read.” Jim Norton says that “you always knew when you were on the show with him that if you weren’t prepared he was just going to run circles around you … because he would embarrass you by just being prepared and funny.” Quinn recalls:

People would just try to mess with him because he was prepared and he was a good … He was the guy that never really let me down. He was the guy that whenever he was on the show, he always had some angle and he never let you down. He never let the show down.

Nick DiPaolo recalls this incident:

I remember him saying to me before an episode of Tough Crowd. I’m writing notes. It’s like an hour before the show. He goes, “DiPaolo, you’re so competitive. Relax,” or whatever. Two minutes before show time, I’m going down the stairs to the studio. He’s under the staircase jotting down notes like two minutes before they’re going to introduce us. I go, “Who the fuck’s competitive, Giraldo?” He was laughing.