David Letterman on Jimmy’s Obsession, Relationship with Howard Stern & His Son Going to College

Dave talks about his son Harry going to college, being an empty nester now, Jimmy being on Monday Night Football, being intimidated by Howard Stern when they first met, their friendship now, Howard sending him a watercolor he painted, his viral interview with Kevin Durant, a very exciting text exchange they shared, and Jimmy’s obsession with him.

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About Jimmy Kimmel Live:

Jimmy Kimmel serves as host and executive producer of Emmy®-nominated “Jimmy Kimmel Live!,” ABC’s late-night talk show. “Jimmy Kimmel Live!” is well known for its huge viral video successes, with over 11 billion views and more than 15 million subscribers on the show’s YouTube channel. Some of Kimmel’s most popular comedy bits include “Celebrities Read Mean Tweets,” “Lie Witness News,” “Unnecessary Censorship,” “Halloween Candy YouTube Challenge,” and music videos like “I (Wanna) Channing All Over Your Tatum.”

[peterfang]

A heartfelt thank-you to Jimmy for bringing Dave back on. Dave is the G.O.A.T and late night hasn't been the same after he retired...

[Lisatruck]

I used to watch Dave late at night with my Dad. We both just loved that show. Dads gone now but everytime I see Dave it brings back memories. Thanks!

[MartinSpitznagel]

It is genuinely touching to see how much Jimmy loves David Letterman.

[jeancameron]

David Letterman never fails to make me laugh out loud. He never changes. He is the greatest!

[courtney]

Been watching Dave for 40 years. Absolutely love that man!

[wildlyunrulyadventures]

My heart!! ❤ David has always been my favorite since I was a small child and he was a weatherman. He still is as quick witted as ever!! Never misses a beat. Still as funny as ever! I love you David. American treasure.

[Pete_Finch]

"This stuff's gotta be true?" Always classic with Dave.

[Joonzi]

Oh wow.. Thank you Jimmy for bringing Dave on.. just seeing him brings back so many memories I honestly get emotional.. Love you Dave. Thank you Jimmy.💙

[blivioniox]

Dave's comedy hasn't skipped a beat. Miss him.

[wewper]

I think a big part of why Dave is a great interviewer is that he is a great guest. It was thrilling to see the give-and-take between these two.

[ladavid]

David Letterman is an icon. A living legend. And despite being passed over as Carson's replacement, history has shown him to be the true king of late-night. 👏

[andrewseow]

Miss late night with Dave Letterman one of the greatest 🥰🥰🥰

[Mattplanespotter]

I used to watch Letterman every night. He came on after midnight here in Australia. Awesome. He is still very sharp.

[SN-szkw]

2 Letterman gigs burned into my mind - the velcro suit toss & his stints as a fast food drive up server. Thank you, David.

[mdouglaswray]

It's funny how Letterman tosses in comedy like seasoning. LOVE IT

[tisdue]

I love Letterman to pieces. Its amazing to see Kimmel's respect and admiration for him too. He was glowing the whole interview.

[Jane-yrcg]

I will never stop being in love with David Letterman!
My mom and I would watch him together years ago when I lived across the street from her, we would talk about him all the time and my son, 4-5 years old at the time, once asked if Dave Letterman was his uncle, he got him confused with his actual Uncle Dave!
We still laugh about that! Now my son will ask if I’ve watched “Uncle Dave” on his YouTube or Netflix show.
We’re 3 generation of David Letterman fans! ❤️🥰

[SoulsInRhythm]

Letterman. Miss him being on TV every day. Simply the best. Hope he's loving life!

[joanneweiss]

What a class act, still & always! Love his Netflix show. Being near his age, literally becoming an adult & parent watching him, this was beautiful. Especially about Harry who definitely has dad's sarcastic brilliant humor!

[eddyballester]

since early 80s viewing his show- stupid pet tricks, top 10s, Bud Melman, Paul and the band of course … thanks so much! Wonderful to recall many of the skits and times…