David Letterman doesn’t retire for another 2½ weeks, but already the accolades are rolling in as fans prepare to say goodbye to the most influential comedian of his generation.
CBS weighs in Monday with a 90-minute special hosted by Ray Romano, but we’ll take this opportunity to trump the network with our own top 10 list, highlighting the very best of Letterman’s 33-year run in late-night television.
10 Get out and stay out (Aug. 31, 1988): Letterman’s intolerance for difficult guests was never more on display then when he banished Harvey Pekar from NBC’s “Late Night” after the comic-book writer rambled on about the host being a corporate shill. “I’m just praying for a terrorist,” Letterman quipped to the audience moments before telling Pekar he had worn out his welcome.
9 They got us, babe (Nov. 14, 1987): A Sonny and Cher reunion may not rank up there with the Beatles getting back together, but there was a sweetness to their joint appearance on “Late Night,” which led to a clumsy but moving rendition of their biggest hit.
8 Charlie’s angel (June 6, 1997): Whether it was Crispin Glover or Joaquin Phoenix (above), no one handled a train-wreck interview better than Letterman. My personal favorite: Farrah Fawcett’s lights-out appearance that the host treated with just the right mix of bewilderment and amusement.
7 Hello, Larry (Nov. 16, 1983): He turned a lot of real-life oddballs into comic foils. The best was Larry “Bud” Melman (Calvert DeForest), a struggling actor whose good spirits and clueless nature would send Letterman into fits of laughter. Melman’s finest moment came when he handed out hot towels at the Port Authority Bus Terminal while yanking the microphone away from passengers’ mouths midsentence. “It’s like a ventriloquist in training,” Letterman said.
6 From the heart (Feb. 21, 2000): Anyone facing a scary medical procedure should take time to re-watch the “Late Show” monologue Letterman delivered after returning from quintuple bypass surgery. “A bypass is what happened to me when I didn’t get ‘The Tonight Show,’ ” said the jovial host in a self-deprecating yet comforting routine that featured a cameo by Jerry Seinfeld.
5 Let’s talk about sex (Oct. 1, 2009): If Letterman ever decides to come out of retirement, he might want to consider opening a public relations firm. After being blackmailed by a “48 Hours” producer, Letterman came clean on the air about having affairs with female staff members, a confessional so direct and honest that it wiped out any serious repercussions. The tactic may have been hard on his family, but fans were quick to forgive.
4 He’ll sleep when he’s dead (Oct. 30, 2002): Warren Zevon was not the biggest musical act to grace the “Late Show” stage, but he was a Letterman favorite, so much so that when he was dying of cancer, the program dedicated the entire hour to him. “Enjoy every sandwich,” Zevon said in a hilarious, touching interview with the most important fan he ever had.
3 Glory days (June 25, 1993): No matter how Letterman decides to leave the air, he’ll have a hard time topping his last show on NBC, which featured a hysterical bit from Tom Hanks on the time he was Slappy White’s bellhop and a surprise appearance from Bruce Springsteen, who had never done “Late Night.” Encore, boys?
2 I wanna hold your hand (April 8, 1986): Before confining himself to the studio, Letterman would often roam the streets of New York, most memorably when General Electric was about to buy NBC. His attempt to deliver a fruit basket to GE headquarters resulted in an absolute refusal by a PR person to shake hands — and one of the biggest laughs in “Late Night” history.
1 New York state of mind (Sept. 17, 2001): As the first late-night host to come back on the air after the Sept. 11, 2001, attacks, the bar couldn’t have been higher for a guy known for cynicism, not sentiment. But Letterman rose to the occasion with an emotional monologue and somber conversation with Dan Rather. As I wrote at the time, Letterman was “strong, shaken, angry, humble, loyal — all the city’s emotions packed into an hour that confirmed Letterman’s place as the proper heir to Johnny Carson’s throne. More important, he stepped up as one of the city’s most eloquent ambassadors.”