Pop Culture

Garry Shandling dies at 66: A look back at the comedian's most memorable moments

Living a life full of career highlights before dying Thursday at age 66, Garry Shandling was both beloved and influential among fellow comedians.

From his reinvention of TV comedy to his scene-stealing moments in blockbuster movies, the stand-up comic, actor and Emmy Award-winning writer made a name for himself with dry wit, sharp writing, anxious antics onstage and an easy-going attitude off it.

Frazer Harrison / Getty Images
FILE - MARCH 24: Comedian Garry Shandling reportedly died today in a Los Angeles hospital. He was 66 years old. HOLLYWOOD - APRIL 26: Actor Garry Shandling arrives at the world premiere of Paramount Pictures & Marvel Entertainment's "Iron Man 2" held at the El Capitan Theatre on April 26, 2010 in Hollywood, California. (Photo by Frazer Harrison/Getty Images)

Countless comedy peers, including Albert Brooks and Jimmy Kimmel, mourned the loss as news spread Thursday afternoon on Twitter.

Although Shandling's life was full of professional accolades and accomplishments — including hosting the Grammys, Emmys and "Saturday Night Live" — here are five of his most memorable.

1. His career-launching stand-up debut on "The Tonight Show Starring Johnny Carson" (1981)

As was often the case during Carson's hosting days, a stellar stand-up "Tonight Show" performance could lead to overnight success and stardom. "I went to the bank earlier today," said the 31-year-old Shandling, while holding a ballpoint pen still attached to a beaded cord. "Have you gotten your free pen yet? These are free. You just yank these things and they pop right out." He'd return to the "Tonight Show" on mutliple occasions, and not just as a guest: He wound up as its fill-in host on multiple occasions.

2. His genre-reinventing Showtime comedy, "It's Garry Shandling's Show" (1986-90)

More than a decade before "Parks and Recreation," "Modern Family" and any manifestation of "The Office" adopted a mockumentary style, Shandling shattered sitcom norms by breaking the fourth wall on his titular TV comedy, whose edited versions later aired in prime time on Fox. The series also featured one of the final appearances by "Saturday Night Live" legend Gilda Radner, who was dying of ovarian cancer. In a later interview, Shandling marveled at Radner, "a woman with that kind of heart, being on the precipice of dying, going on [the] show and saying [the equivalent of] 'Garry, I have cancer. What's your excuse?'"

3. His gut-busting HBO series, "The Larry Sanders Show" (1992-98)

Few TV comedies are as hilarious and as revered as "The Larry Sanders Show," on which Shandling played (and drew from his experiences as) a late-night talk-show host. In addition to a parade of comedy cameos ranging from Bob Odenkirk to Janeane Garofalo, one scene with Sanders (Shandling) and sidekick Hank Kingsley (Jeffrey Tambor) spawned not only lots of laughs, but also the "Hey now!" catchphrase that Howard Stern has used in real life ever since.

4. His scene-stealing movie roles, especially as Senator Stern in recent Marvel blockbusters (2010-14)

Shandling was a welcome sight in many of the movies in which he appeared (or to which lent his voice talents), but two of his final roles were especially enjoyable. As the elected official (and comedic foil) who leads a congressional hearing to investigate Tony Stark (a.k.a. Iron Man) in "Iron Man 2," Shandling reprised his villainous role in "Captain America: The Winter Soldier."

5. His unexpectedly moving appearance on Jerry Seinfeld's "Comedians in Cars Getting Coffee" (2016)

Premiering Jan. 20, the ominously titled "It's Great That Garry Shandling is Still Alive" is full of laughs, but also shows Shandling's pensive side. The two comedians get nostalgic upon their return to the adjacent Hollywood lots where their TV shows were filmed. Shandling looks solemn while reading the neon-emblazoned names of comics surrounding the stage of the legendary Comedy Store, where Shandling got the invitation to do his first "Tonight Show" performance, noting, "It's like every other person has passed away."

He later makes a point to mourn David Brenner and Robin Williams. "That [comedic] material, and your material, is purely a vehicle for you to express your spirit, and your soul and your being," Shandling tells Seinfeld. "It doesn't have any value beyond you expressing yourself spiritually, in a very soulful, spiritual way. It's why you're on the planet." He adds that when a news anchor reported that Williams died at age 63, "I realized, '63 is so young' is a phrase you never hear relative to anything but death."

Replies Seinfeld, "You have to die in your 60s for someone to say, 'Wow, he was young.'"

The video concludes with Shandling's story about an odd interaction with a medical technician. "He said, 'I did a CT scan a year ago of you,'" Shandling recalled. "He said, 'Do you have cancer?' I said, 'No.' He said, 'Oh, good, so you're still alive. I was watching the news, and it seemed like if you'd have passed away, I'd have heard about it on the news.' And I said, 'Well, I don't know, man. I mean, uh, I don't know if they would have broken in or anything.'"

RELATED: In memoriam: 15 celebrities we lost in 2015

Honorable mention: His legacy-affirming stand-up, cheering up Bill Haverchuck on "Freaks and Geeks" (2000)

Shandling's legacy inspired a memorable moment on the celebrated NBC comedy that aired for one season. Set in 1980, the episode "Dead Dogs and Gym Teachers" shows a defeated teenage Bill (Martin Starr) flipping on the TV as the Who's somber "I'm One" plays in the background. But when Bill sees Shandling doing stand-up, the character chuckles, then laughs, then guffaws, all while Pete Townshend sings, "And I can see / That this is me." It's a touching nod to loners and outcasts who found solace in comedy, but also a moving tribute to Shandling himself — and an especially poignant one after his passing.

Follow TODAY.com writer Chris Serico on Twitter.

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