Mad Men may be between seasons, but the drama’s debonair Don Draper, actor Jon Hamm, is seemingly everywhere. He’s signing on to new movies, attending Yankee games with Larry David, and making the entire Internet blush with photos of him wearing, um, clingy pants.

Now, he’s starring in singer Aimee Mann’s new music video, donning a fake mustache and adopting a New Yawk accent to portray a sleazy director. It may seem beneath an eight-time Emmy-nominated A-lister to play a bit part in a music video, but Hamm has a history of making these unusual, surprising, and often fun cameos. Here’s a look back at some of the weirdest and most enjoyable.

1. Aimee Mann’s Music Video

Talk about high concept. The video for Aimee Mann’s new song “Labrador” begins with fake behind-the-scenes interviews with Hamm playing director Tom Scharpling and Mann herself. Hamm-as-Scharpling explains, “What I suggested was, we do a shot-for-shot remake of the Til Tuesday video for ‘Voices Carry.’ She flipped for it.” Mann then clarifies in her fake interview that she did not in fact flip for the idea and is only participating under contractual obligation. The video for “Labrador” that follows is indeed an impeccable recreation of the 1985 clip for “Voices Carry,” making the whole ordeal strangely meta and a bit confusing, but—thanks to Hamm’s committed performance—bizarrely fun.

2. ‘Childrens Hospital’

The Adult Swim comedy Childrens Hospital has gained a swift cult following, thanks to its cast of respected industry heavyweights, including Rob Corddry, Lake Bell, Megan Mullally, and Ken Marino. First appearing in a 2010 episode of the series, Hamm added himself to that list in the most startling of fashions. Buxom star Malin Akerman is delivering a monologue in the season finale when she pulls off a face mask Mission: Impossible style to reveal that she is not Dr. Valerie Flame but Derrick Childrens, the son of the hospital’s founder, played by Hamm with another one of his exaggerated regional accents.

3. Herman Dune Music Video

“Tell Me Something I Don’t Know” is a song by the French folk-rock duo Herman Dune. In the music video, Hamm plays a traveling photographer who makes friends with a tiny blue Yeti. Yep.

4. ‘30 Rock’ Live

It was no stretch to buy Hamm’s performance on 30 Rock as Dr. John Baird, a love interest for Tina Fey’s Liz Lemon who is so devastatingly handsome he goes through life thinking he’s good at everything because he’s too pretty for anyone to put down. Harder to swallow was Hamm’s surprise appearance on last season’s live 30 Rock episode not in his role as Dr. Baird but in blackface as an actor on a retro, offensive, Amos ’n Andy–style show called Alfie and Abner. To say the least, the character was polarizing.

5. ‘A Single Man’

The styling and ambience of Tom Ford’s feature directing debut, A Single Man, so perfectly echoes the moody, smoky stylization popularized by Mad Men that most audiences probably wouldn’t have been surprised had Don Draper himself strolled coolly across the screen. Although Hamm does not share the screen with Colin Firth in the film, sharp-eared moviegoers still get to hear that masculine Draper rasp. Firth’s character receives a phone call relaying heartbreaking news (which won’t be spoiled here), and Hamm, uncredited, provides the voice on the other end of the phone. Not everyone was pleased by the cameo. “It’s an uninterrupted shot, and we should be concentrating on Firth’s powerful reaction,” writes Dan Kois at The Awl, “but instead we are distracted because it is DON DRAPER ON THE PHONE.”

6. ‘Saturday Night Live,’ the LiLo Episode

Jon Hamm has proved to be one of the best modern SNL hosts (hello, Sergio). Any time he stops by Studio 8H should be reason for celebration—unless that visit is all too brief. When the trainwreck of Lindsay Lohan’s “comeback” gig hosting the show first pulled out of the station, the troubled actress began with a monologue making fun of her unreliability, which included the camera panning to Hamm sitting in the audience for a blink-and-you-miss-it sight gag as a “backup host” should Lohan derail. The disastrous performance that followed made fans wish Hamm had stepped in for the starlet, not to mention wonder why he would show up for such a brief appearance in the first place.

7. The New Yorker iPad App

How does one use The New Yorker’s new iPad app? Why not have Jon Hamm explain it to you? Hamm stars in a video directed by and co-starring Girls’ multi-hyphenate wunderkind Lena Dunham as a talk-show host who needs instruction on how to use the app. While no other magazine has found it necessary to draft two of TV’s buzziest stars for a how-to video, the collision of Mad Men, Girls, The New Yorker, and the iPhone is like the seventh level of highbrow heaven.

8. Jimmy Fallon’s Emmy Awards Opening Skit

It’s one thing to merely act in another singer’s music video. But for Jimmy Fallon’s opening skit to the 2010 Emmy Awards, Hamm risked all his Don Draper cool points by agreeing to act, sing, and dance in a parody of Glee. Sure, the likes of Tina Fey and Joel McHale also put their reps on the line to participate in the bit—but so did reality TV pariah Kate Gosselin. The highlight: Hamm doing a “back it up” dance with Betty White.