Top 10 Reasons We Love David Letterman

David Letterman’s career will sadly come to a culmination tonight on CBS. His longstanding career of 33 years as the host of The Late Night Show included various guests from government officials to just about every A-lister out there. Letterman’s style to interviewing was always of a timely tempo, humorous, and comforting. He was also known to always “go there,” with his upfront questions.

He will be greatly missed, and as he finishes off with his 6028th episode tonight, we give you the top 10 things we love about David Letterman.

1. He can hold a conversation with anyone (no matter how difficult)

For David Letterman, being able to talk to anyone comes with the job description—and he does it very, very well. Somehow he can balance a light-hearted chat with everyone from Paris Hilton (his best line: “so, Paris, how’d you like being in jail”) to President Obama, but when actor Joaquin Phoenix appeared on the Late Night Show, Letterman made some hurdles in a very awkward and off-putting conversation (or lack thereof). A curt-spoken Phoenix apparently wasn’t in the mood for Letterman’s witty antics.

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2. He defines norm-core

When Letterman’s not on stage, he’s seen in the quintessential ‘dad-look’: dirty white sneakers, loose khaki pants, and a sports jacket (oftentimes worn with an old graphic t-shirt, presumably from his college days). Perhaps Letterman was was the unlikely muse for the norm-core movement in fashion.

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3. Gap tooth

David Letterman may not be conventionally handsome, but with his ginger hair and wide-grinned, gap-toothed smile, he seems to disarm his guests. Above all, his appearance makes everyone laugh.

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4. He let Dennis Rodman color his hair green

When baller Dennis Rodman appeared on Letterman’s show in 1996, he came equipped—with green hair dye, that is. Rodman who sported a green do himself, felt oh so inclined to give Letterman a makeover, which he graciously accepted.

5. He’s drinking buddies with Betty White

What are Betty White’s hobbies, you may ask? Oh, you know, the usual: gardening, playing with animals, and drinking vodka. So David Letterman unceremoniously pulled out a bottle of Gray Goose and poured two glasses, sending White into an adorable laughing spell (consequently forcing her to spit out her drink while Letterman chugged from the bottle).

6. Because he can handle Madonna’s 14 F-bombs

When an always edgy Madonna (dressed in all black with hair slicked back) appeared on the show in 1994 she was incredibly foul-mouthed, dropping the F-bomb 14 times in a single sitting. This was after she openly admitted to sending her underwear to Letterman prior to the interview. The heat was on from the start, sparked by Madonna’s low-blow comment when she asked if Letterman’s hair was a rug. He refuted by asking if she was wearing a swim cap. By the end of the show, he had to explain that the cussing was too much, “this is American television! People don’t want this in their homes at 11:30 at night,” he said. He was commended with applause.

7. He knows how to deliver a heartfelt monologue

Letterman’s return to television after 9/11 was monumental. In part, New Yorkers depended on him as a kind of ambassador, and needed his consolation (perhaps some relief, too). His delivery was pitch perfect: emotional, empathetic, and yet serious, reminding us of the power of unity.

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8. He’s a flirt

Letterman is always timely—he says the right thing at the right time. Additionally, he loves to dish out the compliments. Where do these gushing, flirtatious comments get him? He scored a lip-lock with Julia Roberts, Gillian Anderson, and Amy Poehler. Not to mention that time he got a glimpse of Drew Barrymore’s boobs or held hands with Maria Sharapova after admitting that he’s 40 years older than her (though they share the same birthday). Here, he’s seen licking Cher’s finger.

9. His awkward laugh (and sound effects)

It’s safe to say that part of Letterman’s charm is his dorkiness, which he knows claiming that “there’s no bigger dweeb than me.” And with that, comes his low-belly cackle, culminated by a screeching, high-pitched “yeeeeeewwww!”

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10. He’s not afraid to get into costume

Letterman has never been afraid to ditch his double-breasted suit for a funny costume. His most memorable looks have included a velcro suit, which he broadcasted while fastened to a velcro wall, and more memorably a puffy, fire-protective getup adorned with marshmallows. His crew torched the suit, roasting the marshmallows for the audience, while Letterman nervously chatted, as usual.

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