Goodbye to David Letterman, one of TV's biggest flirts

Late-night TV has lost one of its favourite ladies' man. The talk show host has charmed the women of Hollywood, rock stars and one Canadian sexpert.
Goodbye to David Letterman, one of TV's biggest flirts

Photo, CBS

Below, a look back at David Letterman's most memorable flirtations, boob-flashes and make-out sessions.

Letterman's ladies

Late-night sex show

Canada’s favourite sex educator Sue Johanson had a fantastic rapport with Dave, both charming and flustering him with questions about his sex life, and by waving sex toys around with abandon. One of the show's favourite guests, she was on six times in five years. It would have been more, but she often told Dave she was too busy talking sex at Canadian high schools and universities to make the trip to New York.

(Credit Image: © Dan Herrick/KPA-ZUMA/ZUMA Press)

Goodbye to David Letterman, one of TV's biggest flirtsSue Johanson

'You're really a handsome woman'

David Letterman sends Julia Roberts a bouquet of flowers every year on her birthday. And on the show he always regales her with sincere compliments: "You're a lovely woman. You're an attractive woman. You're really a handsome woman." The surprising thing is the crush seems to be mutual — and Julia swears she's asked Dave out — and been rejected — twice.

(Photo, CBS)

Goodbye to David Letterman, one of TV's biggest flirtsJulia Roberts

Happy Birthday to Dave

Dave may not approve of Drew's tattoos and tongue piercing, but he can't resist her flirtations. And the time she flashed him, on his birthday in 1995, is high up on his Top 10 list of career highlights.

(Photo, CBS)

Goodbye to David Letterman, one of TV's biggest flirtsDrew Barrymore

Tickle fight

It took Cher four years to agree to come on Dave’s show, and the first interview started off like a bad blind date. Dave opened with "You smell terrific," and a defensive Cher responded, "Is this as good as it gets?" Turns out, they had fantastic chemistry. In one appearance, their banter even led to an uncharacteristic (for both of them) tickle fight.

(Photos, CBS)

Goodbye to David Letterman, one of TV's biggest flirtsCher

Endless kiss

In her first-ever appearance, Dave was fascinated by Gillian's stories of wild teenage years and much-older boyfriends. Years later, they engaged in late night's longest make-out session. But he didn't keep his promise to have her on the show more times than her X-Files costar David Duchovny, who appeared 13 times. (Dave has man crushes too.)

(Photo, CBS)

Goodbye to David Letterman, one of TV's biggest flirtsGillian Anderson

Cute and cuddly

Over the years Dave and Jennifer’s relationship went from fist bumps to snuggling together under a blanket. While Dave does seem concerned with her manic energy, he has a habit of falling for America's sweethearts (see Julia Roberts).

Photo, CBS

Goodbye to David Letterman, one of TV's biggest flirtsJennifer Lawrence

He's with the band

Dave pretty much jumpstarted the Canadian singer's career after he had her on twice in a three-week period for her debut album, Failer. For her third appearance, Edwards took an overnight Greyhound from Ottawa to New York when her flight was cancelled. Later Dave offered to get on a bus for her, hinting at his retirement plans: "From time to time we'll have musical acts on the show and I will travel with the band,” he told Edwards. “I would like to travel with you. So send me an itinerary."

(Photo, CBS)

Goodbye to David Letterman, one of TV's biggest flirtsKathleen Edwards

Click on the pink 'up' arrow to reveal captions. Related: Samantha Bee is crashing the late-night sausage fest Dumping Don Draper: why we’re over TV’s anti-heroes Jane Fonda and Lily Tomlin deserve better than Grace and Frankie


Subscribe to our newsletters for our very best stories, recipes, style and shopping tips, horoscopes and special offers.

By signing up, you agree to our terms of use and privacy policy. You may unsubscribe at any time.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.