It’s no secret that not everyone got along with David Letterman, who has a famously prickly personality. Over his 33 years on late-night TV, he managed to make a lot of his guests pretty angry.

Then again, he was also delightful to many. Here are some of his friends, enemies and frenemies through the years.


* Regis Philbin

Oh, these two. Philbin holds the title for the most appearances ever on Letterman’s late-night shows, as he’s stopped by 136 times over the years. Reege also filled in as guest-host when Letterman had to step off the air for his heart surgery in 2000.

* Zsa Zsa Gabor

You’ll only go on a fast-food road trip with someone you really like.

* Steve Martin/Tom Hanks/Howard Stern/Bill Murray

We group these four together because their interviews seem pretty similar — Letterman is always delighted to chat with other guys who have been around forever.

* Isabella Rossellini

Letterman has always been a fan — remember when he asked her out on a date?
* Denzel Washington

The star has been on the show tons of times and Letterman loves putting him in weird situations: On stage with Don Rickles; telling vacation stories with Lenny Kravitz; trying to start a bromance; or being in front of an empty stage during Hurricane Sandy.

* Jennifer Lawrence

He won’t bring a comforter into the freezing studio for just anyone.


* Cher

We all know she didn’t hold back during this contentious interview.

* Bill O’Reilly

Letterman got actually quite angry during their 2006 talk about the Iraq War.

* Madonna 

Dropping 14 f-bombs in one interview certainly made her an enemy of the network, at least.

* Justin Bieber

He’s just such an easy target.


* Oprah

While they did indeed have quite the awkward interview in the ’90s, talk of their feud may have been a bit exaggerated — by now, they’re actually real friends.

* Lindsay Lohan

Letterman gives her a hard time, but we suspect he has a soft spot for the troubled star.

* John McCain

Never cancel on Letterman with a fake excuse; you will get called out on television. Sen. McCain eventually made up for his blunder by appearing on the show (and apologizing) a few weeks later.


On May 20, David Letterman hosted his last show, ending a 33-year career on late-night television. Here are some of his top moments from CBS's "The Late Show with David Letterman" and NBC's "Late Night." (Jayne W. Orenstein/The Washington Post)