[10] Giraldo passed the bar and began a career as a lawyer, working for eight months as an associate for Skadden, Arps, Slate, Meagher & Flom before changing his occupation.

[11] In 1993, Giraldo provided pro bono defense counsel services to his friend and fellow comedian Jeffrey Ross, who was charged with inciting a riot.

Ross was performing at a comedy club on Long Island when a member of the audience pulled out a toy gun that looked real.

When the case was upgraded to a weapons charge, he had nearly told Ross to plead guilty, which would have resulted in his friend serving jail time.

[25] Giraldo acted in two Adam Dubin features, 2002's comedic short American Dummy, in which he played a psychiatrist, and 2008's animated film, What Blows Up Must Come Down!, in which he did the voice of Jihad Jo.

[28][29] Giraldo also performed at the United States Naval Base in Guantanamo Bay, Cuba, as part of a USO tour in 2002.

His series Friday Night Stand-Up with Greg Giraldo began on Comedy Central in late 2005 and ran until 2006.

Giraldo was featured (along with Dane Cook and Sean Rouse) in Dave Attell's Insomniac Tour, released April 2006.

[25] In 2008, Giraldo appeared in venues across the United States as the headlining act of the Indecision '08 Tour, produced by Comedy Central.

[38] Through the early 2000s, Giraldo was candid about his struggles with drug and alcohol addiction, and the challenges of life on the road, often incorporating these themes into his act.

[12] Earlier that afternoon, he had been scheduled to appear at a concert at the 3rd Annual New York Recovery Rally, introducing singer Courtney Love.

Giraldo was taken to nearby Robert Wood Johnson University Hospital, where he remained in a coma on life support.

[42][44][45] Giraldo was buried at Good Ground Cemetery in Hampton Bays, New York, with the inscription "Beloved Father / Always Loved / Forever Remembered".

[46] John Popper, lead singer of Blues Traveler, dedicated the song "The Mountains Win Again" to Giraldo during the band's concert on September 29; he had worked with the comedian on the TV show Z Rock.

[51] On November 2, 2010, Comix comedy club in New York hosted the Jim Florentine roast, at which Giraldo had been scheduled to perform.

The lineup included sets by Jerry Seinfeld, Lewis Black, Colin Quinn, Dave Attell, Jim Norton, Ted Alexandro, Nick DiPaolo, Jesse Joyce, and Eddie Brill, and the event was hosted by Tom Papa.

[53] Another benefit show was held in Los Angeles at the Wiltern Theater on June 29, 2011, and featured sets by Jeffrey Ross, Daniel Tosh, Marc Maron, Ralphie May, Brian Posehn, Bill Burr, Dave Attell, and Tom Papa; it was hosted by Jesse Joyce.

[54] The Columbia University Alumni Association staged two benefit shows on March 28, 2011, at the Gotham Comedy Club in NYC.

The comedians who performed sets were Todd Barry, Amy Schumer, John Mulaney, Joe Mande, Morgan Murphy, Godfrey, Rachel Feinstein, Michael Ian Black, and Robert Kelly, and the shows were hosted by Gabe Liedman and Stress Factory owner Vinnie Brand.

[55] Seth MacFarlane, Anthony Jeselnik, and Jeffrey Ross paid tribute to Giraldo during the Comedy Central Roast of Donald Trump in March 2011, and dedicated the program to him.

On March 18, 2011, Comedy Central aired Give It Up for Greg Giraldo, a two-hour television special honoring his memory in which multiple comedians, including Jon Stewart, Nick Swardson, Colin Quinn, Jeffrey Ross, Denis Leary, Sarah Silverman, Dave Attell, Tom Papa, Lewis Black, Bill Burr, Daniel Tosh, Chelsea Peretti, Conan O'Brien, Jesse Joyce and Whitney Cummings, talked about his life and career.

[59][60] A biography by Matt Balaker and Wayne Jones, Greg Giraldo: A Comedian's Story, was published in March 2019.

[61] Vice dedicated an episode of its 2022 series Dark Side of Comedy to Giraldo, including interviews with his sons Lucas, Daniel, and Greg Jr.; friends and fellow comics Felipe Esparza, Jim Gaffigan, Tom Papa and Ritch Shydner; talent manager Rick Dorfman; author Matt Balaker; addiction counselor Joe Shrank; and writing and sober partner Jesse Joyce.

[62] Giraldo was universally praised as a brilliant man—his blessing and his curse, said Papa[63]—who took to substance abuse to "quiet the mind chatter.

"[64] When Giraldo compared his career to the success of Larry the Cable Guy and asked for advice on sobriety, Shydner said, "you've got to have acceptance ... you can't outsmart addiction.

[66] Lisa Lampanelli once tried to hide from Giraldo after he said some "mean shit" during one of her roast appearances but, when they saw each other, he kissed her cheek and said, "'great fuckin' job!'