David Letterman’s friends, enemies and frenemies
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.
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?
Jennifer Lawrence
He won’t bring a comforter into the freezing studio for just anyone.
ENEMIES
Cher
We all know she didn’t hold back during their contentious interviews.
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.
This story was originally published May 20, 2015 at 2:13 PM with the headline "David Letterman’s friends, enemies and frenemies."