'Mad Men's '90s Guest Stars Are Proof That For A Show About The '60s, It's Got Millenial Pop Culture Right

While a good many period pieces can be accused of falling victim to nostalgia for the times they’re charged with representing, Mad Men, with guest stars best known for '90s projects, has by and large avoided this transgression. Matthew Weiner’s portrait of the ’60s is anything but hagiographic, picking apart the abjections that lined the evolution of America over the course of the decade. However, though the AMC series might not be imbued with foggy-eyed affection for its contextual era, there does seem to be a separate collection of years that holds a special place in the program’s heart: the late ’90s and early 2000s. At least that’s what we can gather from the virtual assembly line of turn-of-the-millennium pop culture icons brought onto the program in guest starring roles. 

Mad Men’s relationship with millennial pop culture is nearly as interesting as its relationship with the ’60s — and boards a similar M.O. — upturning our images of the child stars with whom we grew up in the same way that it rearranges screen fiction’s standard take on the counterculture age. Weiner borrows very specific images that viewers met anew a decade prior and have relegated to sanctimony in the intermittent years, corrupting them in the same way that he corrupts the sheen so heavily valued by the Sterling Cooper boys.

His appropriation of former child stars — immaculately chosen cult classic embodiments of hope — to roles representing the utmost desperation seems like more than just a lucky juxtaposition. Take Alexis Bledel, known almost exclusively for playing chipper and sweet Rory Gilmore on Gilmore Girls. Three episodes of Season 5 employed Bledel as a depressive housewife, several times the subject of electroshock therapy, clawing at one last glimmer of vivid passion (in the form of an affair with Pete Campbell) before rejecting the possibility of agency altogether and falling wholeheartedly into her black stupor.

Later on, we meet Linda Cardellini, once the folk icon for teenage befuddlement and indefinable frustration, apparently having been drawn asunder by too many summers on the road with Dead Heads. A decade and change after Cardellini showcased high school experimentation on Freaks and Geeks — embodying the sad but vividly alive spirit of most any American child — she appears on Mad Men’s sixth season as an unhappily married neighbor of Don who joins him in the throes of adultery. Less impassioned with the affair than she is simply kept afloat by it. Still as committed to malfeasance as she was back in Detroit, but no longer enlivened whatsoever.

It isn’t only through Don and Pete’s extramarital romances that we see a destruction of the stars and characters we held flawless years back. On the regular ad staff is Trevor Einhorn, likely known best as Frederick Crane on the occasional episode of Frasier. From impeccably earnest beginnings playing the recurring “son” role — one defined entirely by its place as emotional benefactor of the central hero — comes a sardonic and smarmy professional, droll in a fashion that only the summiting cynicism of new adulthood can render.

In less substantial roles, we have former Alex Mack and Bianca Stratford as Larisa Oleynik playing Cynthia, wife of Ken Cosgrove, and Twin Peaks’ Ray Wise as her father Ed, both emancipated from the fantastical motifs that founded their homesteads in the zeitgeist for something all the more chilling: domesticity. 

Whereas guest casting to the degree optimized by Mad Men can be a distracting ordeal, it is that very unavoidable recognition of the stars in question — what’s more, of the roles and themes with which they are most distinctively connoted — that abets every story the show wants to tell with their characters. Weiner’s casting of Bledel, Cardellini, Einhorn, Oleynik, and every other staple of ’90s and 2000s broadcast is to us what the world onscreen is to Don Draper: Something that looks familiar, but suddenly feels altogether different.

Images: AMC (3)

Must Reads