Watch Jon Hamm Try to Convince People to Sleep With Him

(Photo: Billy on the Street)
Should it take this much effort? Jon Hamm and Billy Eichner make their case for a threesome on Billy on the Street. (Photo: Billy on the Street)

Don Draper had no problem getting ladies in the sack, but Jon Hamm has to do a little more convincing.

The Mad Men hunk, 45, again shows his comedic side during a guest spot on the season premiere of TruTV’s Billy on the Street when he and Billy Eichner pound the pavement in the Big Apple to see if strangers will agree to a threesome with them. Eichner, of course, steals the show — partially because he’s so funny and partially because he’s so loud — but this was an especially fun bit because it took quite a bit of swaying to get people to say yes.

Watch the LOL segment, “Would You Have a Threesome With Billy and Jon Hamm?” here:

At one point, Eichner and Hamm, who was rocking slicked-back hair, a wrinkled linen shirt, and five o’clock shadow, approached a woman with the host posing the question. “Very progressive,” Eichner told her of their idea. “I’m gay, you’re black, you’re plus-size, he’s Jon Hamm, he has a SAG Award. It’s all happening.” As if it was scripted, the woman shot back: “He doesn’t have an Oscar though!” Zing.

A few women they approached had to check with their husbands. When one was considering it, Eichner quipped, “He would want you to have a threesome with the star of Mad Men,” though he couldn’t resist noting that Hamm’s star hasn’t has been as bright since the show went off the air in 2015. “I know he doesn’t have great buzz at the moment, but he’s still a handsome fella,” Eichner teased.

Hamm proved he was in on the joke, adding, “Imagine that it was 2009” — two years after the show debuted and its stars were everywhere.

Eichner told this woman that her husband would want her to have a threesome with Hamm — even though he “doesn’t have great buzz at the moment.” (Photo: Billy on the Street)
Eichner told this woman that her husband would want her to have a threesome with Hamm — even though he “doesn’t have great buzz at the moment.” (Photo: Billy on the Street)

Another funny bit was when a woman named Liz said she hadn’t heard of the St. Louis native. D’oh! Eichner offered yet another backhanded compliment, saying, “He has an Emmy Award. Took him seven times, but still he won.” We also got a kick out of the older woman running away from both the men when they approached her, only to pause, turn back, and say she’d sleep with Hamm but not Eichner.

For the record, two men were totally game.

Hamm is single these days, at least publicly, after ending an 18-year romance with Jennifer Westfeldt over the summer. However, relationships are on his mind. In a recent interview with Mr. Porter The Journal, he seemed to change his position on having kids, saying it is now a possibility.

“I don’t think it’s necessarily an imperative. I’m not going to psychoanalyze myself here, but … well, never say never,” he said. “I’ve got nieces and nephews and I’ve been a teacher. I’ve probably been around kids a lot more than all my friends. I feel if you shut that off entirely, you calcify. You turn into that guy.”

As for today, he’s that guy who is trying to convince New Yorkers to have a three-way with him. The full episode of Billy on the Street airs Tuesday when Season 5 of the show kicks off at 10:30 p.m. ET on TruTV.