Oprah makes her last appearance on “The Late Show.” (Jeffrey R. Staab/CBS)

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.

[David Letterman taught us to ward off celebrity stupidity. But stupidity won.]

FRIENDS

* 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.

 

[Stephanie Birkitt has been written out of Letterman’s ‘Late Show’ history, and it’s a damned shame]

ENEMIES

* 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.

 

FRENEMIES

* 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.

 

READ MORE: 

David Letterman retires:  Here’s the most important thing that happened to him every year of his career

Some of Letterman’s best moments through the years

Top 10 parenting lessons I learned from David Letterman

Letterman’s retirement signals a possible generational shift for late-night TV

Here’s what happened the moment David Letterman announced his retirement

David Letterman: 2012 Kennedy Center Honors profile

GALLERY: David Letterman’s late shows

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)