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The '90sest People to Guest Star on 'Mad Men'

By Courtney Enlow | Lists | April 9, 2015 |

By Courtney Enlow | Lists | April 9, 2015 |

He may be the genius behind one of TV’s best shows, but Matthew Weiner is a full-on hashtag ’90s kid. If you had any lingering doubts about that, here are just some of the super ’90s to the max guest stars he’s cast over the years.

Devon Gummersall


As we learned this week, Peggy’s date, the one she might go to Paris with the weekend after next, is Brian Krakow, unreciprocated love of Angela Chase’s life!

Larisa Oleynik


Ken Cosgrove’s wife is Alex Mack.

Bess Armstrong


Angela Chase’s mom totally dropped acid with Roger Sterling.

Joe O’Connor


Clarissa Darling’s dad is also Trudy Campbell’s dad. Clarissa and Trudy are basically sisters.

Dennis Haskins



Charles Shaughnessy


Mistah Sheffieeeeellllllldd was also Saint John (SINJUN, PEOPLE) Powell.

Ted McGinley


Remember that time Ted McGinley tried to have a four-way with Don and Megan? Good times. Al Bundy would likely not approve. Bud probably would, though.

Neve Campbell


Campbell sat next to Don on a plane and talked ashes and spouses, but did not hook up. She got with Skeet Ulrich but not Jon Hamm? Girl needs to talk with her agent.

Kellie Martin


Martin played Betty’s friend and we all felt old.

Marguerite Moreau


Connie from the Mighty Ducks movies played a prostitute. You also know her from Wet Hot American Summer where you wanted her inside you (I mean, hey, what’s up, from before).

Bonus! Trevor Einhorn

OK he’s technically a cast member I believe, not a guest star, but I only just figured out why John Mathis is so familiar to me. And that is because he’s little Joey Thomas from BASEketball. He’s 8 years old and he smells like Robert Downey, Jr.

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