Thirty Something’s Miles Drentell: American Television’s Greatest Bad Guy

Who is the greatest bad guy ever portrayed on an American television show? The first answer to come to the mind of many would probably be JR Ewing of Dallas. But let’s face it, JR was about as subtle as a Scooby-Doo masked villain. Cut me a break.

Those of a certain stripe might suggest Catwoman as portrayed by Julie Newmar. But I’m not talking specifically about the sexiest villain ever, so she’s out.

The Borg? Scary as hell, to be sure, but again not particularly dimensional. And besides, I’m thinking of a human being, not a collective being.

As far I’m concerned the single greatest villain ever portrayed on an American television show was Miles Drentell on Thirtysomething, brought to life by the extraordinary David Clennon. It is far more than a low down dirty shame that Thirtysomething is neither available on DVD nor currently in daily syndication on any major network.

(Instead, we get 72 hours a day of Law & Order reruns.) Thirtysomething was one of the leaders in the golden age of TV drama that marked the mid-80s through the late-90s, along with St. Elsewhere, Twin Peaks, Picket Fences, Deep Space Nine, X-Files, Xena, Buffy the Vampire Slayer and others.

Although knocked as a series about self-indulgent yuppies, the characters on the show were no more self-indulgent yuppies than the equally acclaimed LA Law, and the show was far more interesting than that overrated piece of claptrap. Thirtysomething initially focused on a group of friends in Philadelphia, especially the families of Michael Steadman and Elliott Weston, who ran a small ad agency. But at the end of the first season Michael and Elliott were forced to close down their agency and the next season went to work for a much larger ad agency run by the inimitable Miles Drentell.

Over the course of the rest of the show, most of the best episodes focused on the Faustian relationship between Miles and Michael. Michael tried to be a good liberal, but was constantly torn between his principles and making a living. What some termed a whiny character was actually one of the few characters in television history to suffer genuine angst over the American policy of sucking your principles dry in order for anyone to achieve success in the system of free enterprise.

Miles Drentell suffered no angst. As played by the man who should have had a shelf filled with Emmy awards for the role, Drentell simply reveled in his position as boss-as boss, not as villain. His coolly detached demeanor covered up a Mephistophelian urge to bring Michael over to what appeared to be the dark side.

What made Drentell such a far more fascinating villain than JR was that you were never really sure what Drentell was up to. In the first year that Michael worked there, a character played by the equally brilliant Stanley Tucci was in Michael’s role and over the course of several episodes it was the height of drama to watch as Drentell pitted these two admen against each other in a battle to see who wanted power more.

After that, the focus turned to Drentell’s desire to corrupt Michael. One might well guess that Drentell was simply replaying his own career, that he himself had once been in Michael’s place and played this game with his own Mephisto. Who knows?

The highlight of their relationship-and the series as well-was the two part episode in which Michael and Elliott dared to make an attempt to take the company away from Drentell by working behind his back. This story arc still stands as two of the greatest episodes in the history of American television drama. You watch with an increasing tension in your gut as Michael goes out on a limb to outmaneuver the guy who invented outmaneuvering. Of course, it doesn’t work and Michael is prepared to be fired, but Drentell doesn’t fire him. He keeps him on and even gives him more power. Why?

That’s the beauty of Miles Drentell and why he’s the greatest villain of all time. Drentell had everything he could want: money, power, women. But what did he want more than anything else in life? He wanted to corrupt Michael Steadman. It seemed to be nothing more than a game; there could be some deep psychological reason, but Clennon never played it that way. He always kept Drentell as mystery. And the writers followed suit. One look from Clennon in this role contained more possibilities than all the screen tests for Scarlett O’Hara. He absolutely sunk into this role like he has no other.

It’s quite possible that Miles Drentell is the most fascinating character ever on television, not just the most fascinating villain. Most characters who are villains play themselves as a villain. They revel in their badness like JR. Of course, in real life, villains such as Dick Cheney actual think of themselves as doing good and being good.

With Miles Drentell you never knew. You were never sure if he really thought of his actions as malevolent and enjoyed it, or if he wanted to corrupt Michael not out of badness, but because he knew that the kind of person Michael wanted to be cannot peacefully co-exist within the free enterprise system. No matter what corporate CEOs like to tell you, you can’t be a good human being and a successful producer of profit. It simply cannot be done. And it may be possible that Miles saw genius in Michael. He may have genuinely seen him as his heir apparent and was trying to groom him for the difficult job he knew Michael was unable to handle.

Miles Drentell was playing a game of Faust with Michael Steadman on Thirtysomething, of that there is no doubt. But it’s still unclear whether Miles was working out of evil intentions or good intentions. And you know what they say about good intentions. Unlike just about every other really popular villain in TV history from the one-armed man on The Fugitive to Spike on Buffy the Vampire Slayer (before he got redeemed, of course) Miles Drentell never showed his cards. He never let on what was happening behind that enigmatic smile and those dancing eyes.

And that’s why Miles Drentell of Thirtysomething was the greatest villain ever portrayed on American television show.