With Mad Men well into its final episodes, now is the time to reflect on all the whiskey-fueled adventures of Don Draper and the gang at Sterling Cooper Draper Pryce. Throughout the seven seasons of show, creator Matthew Weiner has unintentionally (or intentionally) cast actors that helped shape entertainment and pop culture through movies and TV in the 90s and early 00s. Here is a helpful guide to those actors, their roles on Mad Men and the shows and movies that you may (or may not) remember them from.
Role on Mad Men: One of the more recent cameos, Gummersall played Steve Wolcott, a nice lawyer who was set up on a blind date with Peggy. After a rough start in the beginning, the two get a little tipsy, have a nice makeout session and plan an impromptu trip to Paris that they probably will never take. He could end up being a repeat character on the show’s last few episodes—and possibly a permanent bedmate for Peggy.
Most notable roles in the 90s: Gummersall played Brian Krakow on My So-Called Life! He was a dork before being a dork was cool. When he wasn’t tutoring Jordan Catalano, he was constantly pining over his next door neighbor, Angela Chase. He also showed up in the lovelorn college drama Felicity as less of an awkward neighbor and more of a college film student that ends up raping Felicity’s best friend… but we’ll forget about that character.
Role on Mad Men: Armstrong played Jane’s (Roger Sterling’s ex-wife) psychiatrist, Catherine Orcutt, who hosts a fancy party that mostly centers on LSD—because no fancy party is complete without psychedelic drugs.
Most notable role in the 90s: Matthew Weiner must have especially enjoyed My So-Called Life because Armstrong played Angela’s uptight mother on the show. Perhaps we’ll be treated to an entire My So-Called Life reunion on Mad Men before the series’ end.
Role on Mad Men: Madame Giselle. Yup. She ran a brothel that Don and the fellas visited. Surprisingly, Don didn’t partake in the infidelity.
Most notable role in the 90s: It just so happens that she is also connected to Devon Gummersall, as she played Felicity’s mom in Felicity. It’s a small television world, isn’t it?
Role on Mad Men: Bledel played Beth Dawes, the wife of insurance salesman Howard, who rode the train with Pete Campbell every morning to the city. She ends up having a pretty intense fling with Pete, but things come to a pretty dark end when her husband decides to commit her for electric shock therapy.
Most notable role in the early ‘00s: The fast-talking, smarty pants Rory Gilmore in The Gilmore Girls.
Role on Mad Men: Danny Siegel is Jane’s cousin and, as a favor to his wife, Roger got him an interview with Don and Peggy. Peggy wasn’t impressed with him, but Don ends up using a tagline he mentions in the interview in a campaign that wins him a CLIO. Don tries to pay him to make it right, but he just wants a copywriting job—and that’s what he gets. Eventually he gets fired—and bounces back big, moving out west to become a big-time Hollywood guy (sort of).
Notable roles in the 90s and ‘00s: In Buffy the Vampire Slayer, he played Jonathan, a member of the villainous “Trio”—although he was probably one of the least evil in the crew. He also showed up in multiple season of Gilmore Girls with Alexis Bledel as Doyle, Rory’s roommate’s boyfriend. Today, Strong is also an Emmy-winning writer and, perhaps most importantly, is one of the people we need to thank for bringing Empire into our lives.
Role on Mad Men: Smith played Nurse Mary in the episode where Betty goes into labor with little Eugene, and has some trippy dreams.
Notable role 80s, 90s, and now: She has been and will be (until the end of time, if we have any say in it) the voice of Lisa Simpson.
Role on Mad Men: Haskins played Phil Beachum, a Cool Whip executive who meets with Don, Peggy and Ken for a tasting session of a new product.
Notable role in the 80s and 90s: The quintessential high school principal that we wish we all had: Mr. Belding from Saved by the Bell.
Role on Mad Men: Aiken played a guy named Rolo, who is a friend of Sally’s brother-like friend, Glen. When Glen comes to visit Sally at boarding school, he brings him, along with some alcohol and cigarettes. When Glen goes off to have some sweet makeout time with one of Sally’s friends, Rolo comes on a little too strong to Sally. Glen finds out and heroically beats him down.
Notable roles in the 90s: The sweet little magician boy in the tearjerking 1998 Julia Roberts/Susan Sarandon vehicle, Stepmom.
Role on Mad Men: Oleynik plays Ken Cosgrove’s overly supportive and encouraging wife, Cynthia.
Notable roles in the 90s: It took me a while to recognize her, but after seeing her in the mid-season premiere I finally said, “She played Julia Stiles’s self-involved sister from 10 Things I Hate About You!” And then it just all started falling into place. She was also the title character of the popular kids series The Secret World of Alex Mack, and had a role in The Baby-Sitters Club.
Role on Mad Men: Martin played Betty’s old friend, Carolyn Glaspie, who brings her family to stay with the Francises. Her older footballing son was pretty stud-like, but it turned out to be her younger, nerdier boy who made Sally feel all tingly inside.
Notable roles in the 90s and ‘00s: In the early ‘90s she was known as Becca from coming-of-age drama Life Goes On and in the later ‘90s well into the ‘00s she was saving lives on ER.
Role on Mad Men: Don Draper’s infatuation with brunettes reached interesting heights with Campbell’s character, Lee Cabot. Don meets her on a flight and learns that she just scattered her late husband’s ashes over Tom Sawyer Island in Disneyland. They share some intimate words, flirtations and she falls asleep on his shoulder. She offers him a ride home with the promise of some sexy time, but Don surprisingly turns her down.
Notable roles in the 90s and ‘00s: She was Julia Salinger in that beloved favorite prime time family drama of the ‘90s that was also often the source of a good cry—Party of Five. Then there was her role as Sidney Prescott in the slasher movie franchise that redefined the genre, Scream And then there was that sweet little flick, The Craft, which you probably (hopefully) still have on VHS.
Role on Mad Men: Cardellini plays Sylvia Rosen, the wife of Don’s neighbor in Manhattan, Dr. Arnold Rosen. Don has an illicit affair with her, of course. They’re finished now, but they recently had one hell of an awkward elevator ride together.
Notable roles in the 90s and ‘00s: In Judd Apatow’s cult TV show, Freaks and Geeks, she was the angsty outcast Lindsay Weir, who popularized the oversized military jacket. She also crossed paths with fellow Mad Men guest star Kellie Martin on ER and now stars in the Netflix series Bloodline.