Conan O'Brien isn't a regular boss. He's a cool boss!
"We found out that she has a Zoom cocktail party every now and then during the quarantine and that she's having one any second now," he said, explaining that Kelly was in on it but her friends weren't. "So, what I want to do is Zoom bomb our producer Kelly Smith's cocktail party because it's her and a bunch of ladies, maybe a dude or two, hanging out and talking about young people stuff. Swiping left, swiping right, hashtags, you know, whatever they—Coolio get the stretch. I don't know what kids talk about, but I want to find out."
But before hilariously crashing the happy hour, Conan needed to dress the part. Donning a hoodie and a baseball cap that he wore to the side, he joked, "Bang, look at me. 25. 26. Who would know the difference?"
As he joined the chat, viewers were able to get a preview of what the pals were discussed before his epic Zoom bomb. "To me, Clayton is, like, the most beautiful man alive. I mean, I'm just like, ‘Why are you gay?'" one friend said as she poured herself a drink, followed by another one, who said, "Wait, I was gonna replace simple syrup with that agave, so…"
Much to Conan's surprise, Kelly and her friends were thrilled to see him enter the Zoom call. "Ladies, what's the hot goss?" he said after being welcomed into the video chat. "Happy quarantine! I just want you guys to imagine that I'm your age and we're just hanging out and we're gossiping."
Curious to know more about what the funnyman was drinking, one friend made some small talk with Conan. "I like a buttery [chardonnay] and then I like to watch Say Yes To The Dress," he replied as more of Kelly's friends joined the chat.
After meeting the late night producer's couple friends, Conan took it upon himself to share the dating advice that he's given her. "I've tried to give her dating advice, which is to get to the clubs early," he told the excited group. "Kelly, if you go early, they don't run out of glow sticks. You get your drink, you get all set up and then it's always good to be home by 10."
His advice backfired when Kelly quipped, "Listen, we've talked to about this many a-times before and you still haven't introduced us to any hot celebrities." Firing back, he joked, "But, wait. I tried to—I gave you Gary Busey's phone number."
But, unfortunately for Conan, things took a turn when he let it slip that Kelly had briefed him on each of her friends ahead of the call. Watch his hilarious Zoom bomb unfold in the video above!