David Letterman’s Top 10 Crazy Moments
Including Tina, Drew, Madonna and, oh yeah, Richard Simmons
Well, folks, this is it. On Wednesday, David Letterman blows his final kiss goodnight.
He’s been a New York broadcast staple for 33 years. His three shows have been nominated for 112 Emmys, he’s welcomed nearly 20,000 guests on his stages and he’s had more outrageous moments than one could even count.
So instead, we compiled our own “Top 10 List.”
#10: TINA FEY STRIPS DOWN TO HER SPANX
Let’s kick things off with a little ditty from just a couple weeks ago. Ultimate, all-time girl crush Fey stops by for her final Late Show appearance and manages to perfectly flirt and self-deprecate at the same time.
#9: BETTY WHITE CHUGS BOOZE
When asked what she does in her free time, White quips: “Vodka’s kind of a hobby.” So naturally, Letterman busts out the Grey Goose.
#8: JENNIFER LAWRENCE BECOMES OUR BESTIE
By 2013, the Hunger Games actress had been in the spotlight for about three years. But her “you can only s#&! your pants so many times a day” confession solidified her as America’s new sweetheart.
#7: BILL MURRAY ARRIVES AS LIBERACE
Fun fact: Murray was Letterman’s very first Late Night guest in 1982, so for the 20th-anniversary show, Murray got a little fancy.
#6: PETER O’TOOLE RIDES IN ON A CAMEL
It’s not just the mode of transportation that the esteemed actor chose for this London-taped show; it’s how he rewarded said transportation after.
#5: RICHARD SIMMONS SETS A VEGGIE STEAMER ON FIRE
A show regular, the flamboyant fitness legend has had his fair share of funny clips over the years. But accidentally exploding an appliance takes the fat-free cake.
#4: HOWARD STERN DRESSES IN DRAG
During his shock-talk heyday, another show regular went in full theme to promote his book Miss America.
#3: JOHNNY CARSON DROPS BY
The former Tonight Show host (and Letterman’s personal idol) made a surprise, speechless appearance in 1994 (met with audience pandemonium). It would turn out to be his last on television.
#2: MADONNA CAN’T STOP DROPPING F BOMBS
We’ve spared you of some of the more uncomfortable forms of outrageousness (looking at you, Joaquin Phoenix). But a saucy 1994 Madonna slipping 14 expletives on network TV (the most censored interview in history at the time) can’t not be included.
#1: DREW BARRYMORE FLASHES DAVE
Oh, 1995. A time of shaggy bobs, baby tees, bare midriffs and, um, Barrymore’s wilder days. This is easily the singular clip synonymous with Late Show.