Watch 5 of the Weirdest Moments on Letterman

April 29, 2015 Updated: July 18, 2015

David Letterman, late-night TV host and funny man, is calling it quits after 33 years. He will retire from his namesake show on May 20.

Letterman talked about his career—the highs and lows, the stupid and the weird—in an interview with the New York Times.

In recalling his early years as a young late-night host, Letterman reflected on all of the restrictions placed on the late-night landscape. “I never knew if the stupider things we did or the more traditional things we did would work,” he quipped in the article. In the end, he realized what worked best were the weird things.

Here are five weird moments on Letterman’s show:

For a treat, this little talking dog will say Obama.

Crispin Glover shows Letterman how high he can kick in this hilarious clip.

Lindsay Lohan sheds some tears during this somewhat awkward interview.

Why does Letterman keep telling Joaquin Phoenix what a great actor he is?

Robert Downey Jr. seems to feel a little uncomfortable giving advice, but Letterman manages to coax it out of him.