David Letterman hung up his boots last night after 33 years presenting Late Night, and yes, we don't get him over this side of the pond but there's no denying that the man is a broadcasting legend, wherever you are talking about him.

Some of Hollywood's biggest stars have joined the host these past few weeks to pay tribute to the broadcasting master, all making for some great interviews, between Tina Fey stripping and Bill Murray popping out of cakes.

However, the host is no stranger to these unique yet hugely entertaining interviews with some of Hollywood's greats popping by for a chat down the years, so we put together a list of the top five most iconic interviews for your viewing pleasure.

1. Drew Barrymore (1995)

Twenty years ago, a bright eyed and bushy tailed Drew Barrymore was so delighted to hear that it was David Letterman's birthday, she jumped up on his desk and flashed him, no less. Sure where would you get it?

2. Madonna (1994)

We're not sure how Madonna even fitted into the studio back in '94 with the gigantic chip on her shoulder. She sat there smoking her cigar, cursing, and slagging off Letterman, he was well able for her though. However, it would take another six years for her to appear on the show again. Watch the awkwardness/brilliance unfold below;

 3. Joaquin Phoenix (2009)

Nowadays, this bearded Joaquin would be globally accepted as an uber-trendy hipster type, back in 2009 though, he was just one gigantic beardo. He appeared in this now infamous interview with Letterman where he discussed his retirement from acting as he wanted to start a rap career. Yep. However it later emerged it was a publicity stunt for his mockumentary film with Casey Affleck called 'I'm Still Here', while he also apologised for his mad behaviour in an interview on the show in 2010, but thanks to the interweb, we can relive it forever.

4. Oprah Winfrey (2005)

Oprah and David had a notorious sixteen year feud which ended with this interview back in 2005. Apparently, it started when David and his girlfriend decided to skip out on a bill, tricking the waiter into thinking Oprah agreed to pay it. Clearly, you should never mess with Oprah. The pair finally buried the hatchet in this interview which basically is just one big love-in for the pair, or 'the Super Bowl of Love', as Letterman jokingly referred to it as.

5. Bill Murray (1982)

David Letterman's first ever guest was the legend that is Bill Murray, who also had the honour of being one of his last. Since this, the star has been on the show more than twenty times, in many a memorable interview, but this was where it all began. When a young Bill Murray showed up to NBC and made quite the impression when he spray-painted "Dave!" in front of his desk and finished the interview by rocking out to Olivia Newton John’s 'Physical' with aerobics.