Colbert and Letterman Launch Objects Off a Roof at CBS Bullseye

Stephen Colbert’s tenure as host of The Late Show is wrapping up next week due to “financial reasons,” and it has nothing to do with his playful digs at former President Donald Trump. To mark this occasion, Colbert welcomed the show’s original host and creator, David Letterman, for a memorable chat and some rooftop antics.

During the May 14 episode, Letterman and Colbert took to the roof of the Ed Sullivan Theater to hurl actual CBS property, including chairs, off the edge and onto the street below. It was a blast, with the duo aiming for a large CBS logo on the ground, making it clear that their feelings toward the network were less than favorable.

If you’re not familiar with Letterman or his legacy on The Late Show, you might wonder why they engaged in this rooftop throwing spree, aside from the sheer fun of it. This act is a nod to the countless times Letterman and his crew tossed random items off tall buildings, including their own theater in NYC. This bit was so beloved on the original show that when Colbert took over, the network cautioned him against continuing the tradition.

“This is a true story,” Colbert shared. “When I first got this gig, one of the first things they told me before we even moved into the offices was that I wouldn’t be allowed to throw anything off the roof of the Ed Sullivan building, because evidently there was a problem with a previous tenant. I never did it, but we’re at the end here, so all bets are off.”

And yes, they even dropped some watermelons from the roof. Watching Letterman toss items off the building stirred up a wave of nostalgia and warm feelings.

One observer, Jesse Thorn, host of NPR’s Bullseye, expressed his emotions on social media: “I started crying this morning watching Letterman and Colbert throw watermelons off the roof of the Ed Sullivan Theater. How is your day going?”

While I didn’t shed any tears, I felt a surge of emotion watching two legends toss a chair off a building. Nowadays, similar content is often served up through algorithms on vertical scrolling video apps, sandwiched between ads for cryptocurrencies and loud pitches from enthusiastic hosts. But back in the day, this kind of fun was just part of the network TV experience, feeling a lot more wholesome and genuine.