In Character: Stephen Tobolowsky

One of the things I love most about character actors is that the great ones really can play anything. Stephen Tobolowsky is a perfect example. Looking through the roles I’ve highlighted below, there isn’t a common thread among them. We have psychopathic murders, goofballs, straight-laced business exe­­cs, zany film producers, and so on. The man has 232 IMDb credits, most of which defy the notion of typecasting. Very few of his best roles are alike, but damn near all of them are enjoyable. Stephen Tobolowsky is one of the best, most recognizable character actors currently in film. Below are just six of many reasons why.

Five Essential Roles

Mississippi Burning (1988)

Clayton Townley

Stephen Tobolowsky has played a lot of assholes, but few of them rival Clayton Townley. For the purposes of Mississippi Burning, Townley was based on Samuel Bowers, the founder of one of the KKK’s most violent chapters. Tobolowsky’s incarnation of Townley is cold, calculating, and smartly two-faced. He’s expert at denying any of his wrongdoings to the press, but behind closed doors, he reveals himself to be a callous monster. Clayton Townley was one of Tobolowsky’s first film roles, and looking back now (after the actor has had such a prolific career), it’s great to see that Tobolowsky always had it.

Groundhog Day (1993)

Ned

We’ve all known guys like Ned. Guys who are so ceaseless with their optimism that we actually try to avoid them. Passing him on the street day after day would be hard enough, but the fact that Phil Connors has to endure a “new” introduction to Ned every single day must be pure hell.

Groundhog Day is so accomplished because it manages to make good use of repetitiveness. Seeing the same things (and meeting the same people) over and over should grow tired at some point. Yet it never does. Tobolowsky essentially repeats variations of the same few sentences in this film, but it is hilarious every time he does it. The best, of course, being when Ned reacts timidly to being hit on by Phil. The way Ned scurries away down the sidewalk never fails to crack me up. “Bing!”

The Insider (1999)

Eric Kluster

As the president of CBS News, it is Eric Kluster’s ultimate decision to alter what will be one of 60 Minutes’ most controversial segments. 60 Minutes recently interviewed Dr. Jeffrey Wigand, a scientist who broke his confidentiality agreement with his former Big Tobacco employer, so he could blow the whistle on their practices. But with the tobacco company threatening legal action against CBS if they run the segment, Kluster decides to air a heavily doctored version of the show, leaving CBS out of risk. This infuriates 60 Minutes producer Lowell Bergman (Al Pacino), who lashes out at Kluster, essentially calling him a greedy coward.

Now, Tobolowsky isn’t in The Insider for very long, but there’s an exactitude to his language that I absolutely love. Guarded by a thick beard and a smug smile, Kluster is a guy with his finger on the trigger, only he’s too afraid to pull it. It’s also worth noting that Tobolowsky takes a verbal beating in a way that few are able to do. He gets his ass thoroughly chewed out by Pacino and Christopher Plummer in this movie, both times trying so hard to keep his dignity intact. If only.

Entourage (2007)

Mayor of Beverly Hills

Stephen Tobolowsky has delivered dozens of one episode arcs on popular TV shows, but his brief stint on Entourage is my favorite. Johnny Drama (Kevin Dillon) lives right on the edge of Beverly Hills, and if he takes the Mayor of Beverly Hills out for a night on the town, the Mayor will annex Drama’s condo, giving Drama a 90210 address. So the boys hit the town, with the intention of having superstar Vincent Chase (Adrian Grenier) pick up chicks for the Mayor. If you’ve seen this episode of Entourage (Sorry, Harvey – Season 4, Episode 4), then you know how the Mayor’s night ends up. But for those who haven’t, believe me, few things inspire as good a laugh as Stephen Tobolowsky cruising Beverly Hills in a ridiculous Ed Hardy shirt, doing his damndest to swoon exotic European women. Truly, the final scene of this episode is one of my all-time favorite Entourage moments.

Californication (2011-2014)

Stu Beggs

Stu Beggs is arguably Stephen Tobolowsky’s most outlandish character. He’s an insanely wealthy, hard living movie producer who cares little about what other people think. Stu is the kind of guy who not only tries to woo the wife of one of his closest colleagues, but he actually asks the colleague if it’s okay first. Upon receiving said colleague’s approval to go after his wife, Stu returns the favor by hooking the colleague up with a bimbo on Stu’s staff. So that’s who Stu Beggs is.

I haven’t seen every episode of Californication, but as I slowly make my way through the series, I can happily admit that the show was given new life in Season 4 with the introduction of Stu Beggs. Tobolowsky remained on the show for the rest of its run, which leaves me so eager to see what kind of crazy shit Stu Beggs still has to get into.

The Best of the Best

Memento (2001)

Sammy Jankis

I’ve always loved Stephen Tobolowsky’s work in Memento. But I have a newfound appreciation for it, having recently learned that Tobolowsky himself considers Sammy the most difficult role he’s ever played. When speaking with the A.V. Club a few years ago, Tobolowsky said that Sammy had no lines in the script for Memento. Instead, Christopher Nolan encouraged Tobolowsky to improvise his dialogue. A tough feat, given that Sammy is essentially a man with no memory. “Part of my brain had to remember what it was doing, and another part had to not remember what I was doing,” Tobolowsky said. For an actor, that’s a damn difficult world to live in. But obviously Nolan’s methods paid off, as Sammy represents the most evocative work Tobolowsky has delivered yet.

The scene in which Sammy’s wife “tests” Sammy’s condition is one of the most shocking moments in the film. The arc Tobolowsky hits – from fond appreciation to utter indifference to scared shitless puppy dog – is rather miraculous. It’s a great and haunting moment in a great and haunting film. Pure conviction, made up on the spot. That’s the work of a stellar actor at play.

Other Notable Roles

in Spaceballs

Spaceballs (1987)

Two Idiots in Hollywood (1988)

Great Balls of Fire! (1989)

Bird on a Wire (1990)

Mirror Mirror (1990)

The Grifters (1990)

Thelma & Louise (1991)

Single White Female (1992)

Sneakers (1992)

Basic Instinct (1992)

Hero (1992)

Calendar Girl (1993)

Murder in the First (1995)

The Prime Gig (2000)

Love Liza (2002)

Freaky Friday (2003)

CSI: Miami (2003-2005)

Curb Your Enthusiasm (2005)

Stephen Tobolowsky’s Birthday Party (2005)

Deadwood (2005-2006)

John from Cincinnati (2007)

Heroes (2007-2008)

Glee (2009-2011)

Justified (2012-2013)