Its 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. Herearesome of hisfriends, 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 Lettermans late-night shows, as hes 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
Youll 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 interviewsseem 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 timesand 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 wont bring a comforter into the freezing studio for just anyone.
[Stephanie Birkitt has been written out of Lettermans Late Show history, and its a damned shame]
ENEMIES
* Cher
We all know she didnt hold back during this contentious interview.
* Bill OReilly
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
Hes 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, theyre 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: Heres the most important thing that happened to him every year of his career
Some of Lettermans best moments through the years
Top 10 parenting lessons I learned from David Letterman
Lettermans retirement signals a possible generational shift for late-night TV
Heres what happened the moment David Letterman announced his retirement
David Letterman: 2012 Kennedy Center Honors profile
GALLERY: David Lettermans late shows
On May 20, David Letterman will host 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)
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Source: http://www.washingtonpost.com/blogs/style-blog/wp/2015/05/19/david-lettermans-friends-enemies-and-frenemies-through-the-years/
