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The Second(-Billed) City: 19 great Chicago character actors

From left to right: Joe Mantegna, Tim Meadows, Joan Cusack / Graphic: Nick Wanserski
From left to right: Joe Mantegna, Tim Meadows, Joan Cusack / Graphic: Nick Wanserski

Chicago is a “that guy” kind of town, its very history shaped by political machines and criminal syndicates whose leaders all resembled character actors of one type or another. It’s also home to venerable ensemble theater companies such as Steppenwolf and improv comedy institutions like Second City, which has made it a crucible of talent that’s produced scene stealers on screens big and small. Mind you, Chicago and its suburbs have produced plenty of big stars with local roots—your Harrison Fords, your John Malkoviches, your John Cusacks, your Jennifer Hudsons, your, uh, Jim Belushis. But our metropolis of underdogs has a deep self-identification with the perpetually second- and third-billed, the sort of hometown pride that could make Dennis Farina a bona fide local celebrity and inspire a popular Italian beef joint to plaster pictures of Joe Mantegna on its wall. As part of The A.V. Club’s weeklong tribute to its home base, here is a guide to some of our favorite Windy City character actors, whose presence always brings something real—something ineffably Chicagoan—to whatever project they turn up in.

1. Joe Mantegna

With a mug and a rasp that’s lent itself to heavies hailing from Little Italy, Hell’s Kitchen, and, er, Springfield, Joe Mantegna’s Chicago roots don’t immediately reveal themselves—until, say, he drops the “whud an ahn-err” at the top of his Saturday Night Live monologue from 1991. In that monologue—which starts with Mantegna apologizing for not being Hall Of Fame quarterback Joe Montana, before going somewhere much, much darker—Mantegna admits he’s not the first name that leaps to mind in relation to comedy. But his body of work says otherwise, his knack for pivoting between crime epics and Billy Crystal rom-coms honed on the training ground of the Chicago stage. He paid tribute to the always-down-but-never-out denizens of Wrigley Field with 1979’s Bleacher Bums before breaking out as ruthless real-estate salesman Ricky Roma in the original Broadway production of Glengarry Glen Ross. But there’s a soulfulness to Mantegna that makes you want to trust the characters he plays, something that’s come in handy as he’s matured into the gruff department head on a certain CBS procedural. [Erik Adams]

2. Joan Allen

Joan Allen took up with the Steppenwolf Theatre Company back in 1977 at John Malkovich’s behest, which led to a critically acclaimed turn in And A Nightingale Sang. While that decades-long partnership alone could serve as Allen’s Second City bona fides, she doubled down by appearing in Manhunter alongside fellow Chicago folk William Petersen, Dennis Farina, and director Michael Mann. Allen’s Pleasantville character is probably her most “Midwestern” role to date: kind, good-natured, and corn fed. The turmoil that’s just under the monochromatic surface is symbolic of the wonders that are all too often hidden by a blanket of snow in this Midwestern metropolis. But it’s the Rochelle, Illinois, native’s versatility that speaks to her roots: She’s as much fire and ice as Chicago is. Allen’s played flinty authority figures in the Bourne films and Death Race as well as a woman who discovers The Upside Of Anger when her life falls apart. Later, she combined her vulnerability and patrician features for her role as Pat Nixon opposite Anthony Hopkins in Oliver Stone’s Nixon. Allen recently starred as the overly ambitious matriarch of ABC’s The Family, but although that series was ultimately short-lived, she still managed to turn up the heat behind an icy stare. [Danette Chavez]

3. William Petersen

A character actor who’s also a leading man, Evanston-born William Petersen is the definition of cult appeal. In Chicago—where they call him “Billy”—he’s a living legend, a veteran of the Goodman, Victory Gardens, and Steppenwolf theater companies who co-founded his own hot-shit ensemble, Remains Theatre, in the late ’70s. (It disbanded in 1995.) Petersen’s theater colleagues even cheered him on when he made the leap to Broadway in the ’90s, temporarily setting aside the distrust for all things New York-related that is the natural instinct of Chicagoans. Meanwhile, Petersen’s TV and film career is full of near-misses and after-the-fact successes. He starred as a cop in Michael Mann’s Manhunter and William Friedkin’s To Live And Die In L.A.; both films have since been reappraised, but their lukewarm reception at the time of their release meant that Petersen’s career as a movie star never really took off. Instead, after flitting from theater to TV to film for a few decades, he spent nine years in the procedural salt mines in yet another detective role on CSI: Crime Scene Investigation. His intense screen presence might lead you to believe that Petersen is as obsessive as his characters, but in real life, he’s a typical Chicago boy; even though he moved to Los Angeles years ago, Petersen still roots for his beloved Cubs and has narrated three different documentaries about the baseball team. When the Cubs finally won the World Series last year, Petersen’s response got its own article in the Chicago Tribune. [Katie Rife]

4. George Wendt

Although George Wendt’s most prominent role is inextricably linked to a New England city, the actor is pure Chicago. The Beverly native bounced around a couple of colleges (including Notre Dame) before working at the Second City in the ’70s, where he developed a lifelong relationship with comedy. Wendt went on to play Norm Peterson on Cheers for 11 seasons, during which time he became one of Boston’s most quotable fictional citizens. But he also parlayed his real-life love of the Chicago White Sox and Bears into a recurring gig as one of Saturday Night Live’s Superfans. The sketches saw Wendt don an orange-and-blue jersey and swig beers to toast “da Bears” alongside fellow Second City alums Mike Myers, Chris Farley, and Robert Smigel. Wendt’s culinary preferences and nearly consonant-less sentences denoted a certain type of South Side denizen, but even his non-Superfans roles saw him capture the indomitable spirit of this city. Throughout the years, Wendt has also teamed up with Stephen Colbert, another Second City grad, making guest appearances on the latter’s talk shows. Wendt recently returned to the stage as Northlight Theatre’s Funnyman. [Danette Chavez]

5. Amy Landecker

Amy Landecker’s name is inherently tied to Chicago, as her father is John “Records” Landecker, a well-known DJ who ruled the Windy City radio airwaves for decades. Amy Landecker took advantage of the multitude of great theater in her hometown, appearing at Chicago’s Steppenwolf, Goodman, and Victory Gardens theater companies. She also appeared in hundreds of voice-over roles, having inherited her father’s gift for audio work. She’s come into her own on screen recently as the eldest daughter on Amazon’s compelling family dramedy Transparent and has been a welcome addition to several other TV productions—as a gullible psychiatrist on Revenge, a crush on Curb Your Enthusiasm, even Louie’s mom on Louie—as well as prestige indie movies like Enough Said and A Serious Man. Her no-nonsense Midwestern persona helped her break through to blockbusters in this year’s Doctor Strange, which we suspect is only the beginning of larger things from Landecker. [Gwen Ihnat]

6. Tom Berenger

Based on the roles he’s best known for, you’d be hard-pressed to find a more apt Midwestern everyman than Tom Berenger. From the Michigan-bred Hollywood actor he portrayed in The Big Chill to his turn as the washed-up journeyman catcher of the Cleveland Indians in Major League to his actual upbringing in Chicago’s southwest suburbs (likely what gave him that Southern twang), he’s a virtual stand-in for all the flyover states. Berenger could play anyone who grew up between the Cuyahoga and the Mississippi, but it’s likely his role as Sgt. Robert Barnes in Oliver Stone’s Platoon that pigeonholed him as a tough guy of the highest order (it also earned him an Academy Award nomination). He’d end up playing some variation on this twisted military vet the rest of his career: Born On The Fourth Of July, The Substitute, and Sniper (a whopping four times). Even more recent turns in Training Day and Inception have proved that age won’t derail this Chicagoland native from providing both gruffness and gravitas at a moment’s notice. [Leonardo Adrian Garcia]

7. Tim Meadows

The running gag during Tim Meadows’ 10 seasons on Saturday Night Live was that Tim Meadows was still on the show. It’s a bum rap for a guy who’d risen risen through the Chicago Second City ranks alongside Chris Farley and Bob Odenkirk, then weathered some of the roughest patches of SNL history, eventually landing a signature character in call-in show lothario Leon “The Ladies Man” Phelps. Leon got the spin-off movie, but it’s the work Meadows did as a utility player and consummate straight man—his performance as a no-nonsense census worker opposite an unhinged Christopher Walken, or his infectiously giddy pitch work for “Shirt In A Can”—that’s defined his post-SNL career. Mean Girls and Walk Hard: The Dewey Cox Story are two of the most quotable film comedies of the 21st century, but they wouldn’t be nearly as quotable without Meadows’ poker-facing his way through Dewey Cox’s introduction to pot or a report that Regina George and Aaron Samuels were seen canoodling at Chris Isen’s Halloween party. In recurring roles on shows like Son Of Zorn, The Goldbergs, and Bob’s Burgers, meanwhile, Meadows mines outwardly square characters for subtle eccentricities. [Erik Adams]

8. Michael Shannon

Michael Shannon is currently Hollywood’s go-to weirdo, known for his striking intensity that’s only heightened by his harsh features. Through his Oscar nominations, his stint on an HBO prestige drama, and his turn as a villain in a superhero movie, Shannon has repeatedly made pilgrimages to Chicago, specifically to A Red Orchid Theatre, which he co-founded. As he racked up bit parts in the likes of Groundhog Day, Shannon’s career flourished on the Chicago stage, where he worked alongside Tracy Letts, whom he calls his “greatest mentor.” Letts, both actor and playwright, provided Shannon with juicy roles in his horrifying studies of the human psyche Killer Joe and Bug, the latter of which became a William Friedkin film that starred Shannon. One of the industry’s greatest true eccentrics, Shannon approaches all of his performances with an experimental spirit and an incredible loyalty. Just look at his projects with Jeff Nichols, a director attuned to the humanity in his bizarre persona. [Esther Zuckerman]

9. Matt Walsh

Improv comedy is a distinctly Chicago art form, its various arcane rules and rituals sketched out in smoky dive bars and cramped Clark Street theaters by gurus like Del Close and his rotating cast of “yes and” acolytes. Among Close’s latter-day students is Matt Walsh, known in the improv world as one of the near-legendary founders of the massively influential Upright Citizens Brigade and to everybody else as the guy who shows up for a couple of minutes in the Hangover movies and to say some of the mean, funny stuff on Veep. Walsh’s movement from improv incubation into the national spotlight has been a slow one, starting with the UCB’s Comedy Central sketch show and quick conceptual weirdness on Late Night With Conan O’Brien. But more and more funny filmmakers—David Wain, Todd Phillips, and Will Ferrell, to name a few—have started to recognize how much a quick dose of Walsh’s blend of game acceptance and slowly simmering fury can add to a flagging scene. (So did Emmy voters, who granted him his first nomination last year for his work as befuddled-but-angry press secretary Mike McClintock on Veep.) But his hard-earned Hollywood success hasn’t disconnected Walsh from his Midwest roots; for years now, he’s been keeping in touch with his Chicago side with a series of UCB-hosted sports podcasts, most notably Bear Down, named in honor of his beloved Chicago Bears. [William Hughes]

10. Dennis Farina

When the Chicago-bred Michael Mann, ever a stickler for authenticity, was researching his debut feature, Thief, he consulted with Dennis Farina, a local cop in the city’s burglary division. Mann got more than just good advice: After casting Farina in a small part as a henchman, he found one of his most valuable players, kicking off a collaboration that would see Farina taking key roles in the director’s Manhunter, Crime Story, and Miami Vice, and launching a long, fruitful career with Farina playing both sides of the law. The gravelly voiced, frequently mustachioed, gruffly lovable Farina (who died in 2013) played an endless assortment of cops and mobsters across films like Get Shorty, Snatch, and Out Of Sight, while his TV résumé included everything from the requisite two seasons on Law & Order to guest shots on New Girl to a stint hosting Unsolved Mysteries. But no matter the role—whether he was committing, investigating, or simply reporting the crime—Farina maintained a recognizably Chicagoan pugnaciousness, a ya-gotta-be-shitting-me sense of humor, and an inborn gift for swearing that made even his most intimidating threats a joy to watch and lent legitimacy to every project lucky enough to have him. [Sean O’Neal]

11. Joan Cusack

Joan Cusack is often paired with her brother, John, but the sibling matchup may be doing her a disservice, as it fails to play up her remarkable versatility. Although she received an Oscar nomination for playing the wacky best friend in Working Girl (followed by a similar sidekick role to Julia Roberts in Runaway Bride), this Chicago resident has shown for years that she’s so much more than that. She’s played everything from an Addams Family paramour to a buttoned-up School Of Rock principal to an offbeat nurse who saves a family in Men Don’t Leave and a beloved Toy Story heroine. Even her early movies as a teenager in My Bodyguard and Sixteen Candles reveal the sweetness inherent in every role she takes on. Cusack’s uniqueness—her height, her voice, that shock of red hair—makes it difficult to take your eyes off of her when she’s on screen, which is why she makes the most out of blink-and-you’ll-miss-them roles, like Blair in Broadcast News and Franny in Friends With Money. Her sitcom What About Joan? didn’t pan out, but we give her props for attempting to film it in Chicago. Although she seems to personify “utility player,” we’d love to see her attempt another lead role of her own. [Gwen Ihnat]

12. Michael Madsen

You hack one guy’s ear off, and people think they know you. Such is the case for Michael Madsen, an actor who trained as an apprentice to John Malkovich at Chicago’s Steppenwolf Theatre Company and has published several books of Beat poetry, but who will always be the soft-rock-loving psychopath Mr. Blonde in 1992’s Reservoir Dogs. Madsen had made an impression with his tough yet sensitive role in Thelma & Louise, but—following a string of playing other arrogant, dangerous men in The Natural and Kill Me Again—Quentin Tarantino’s cult hit cemented Madsen as a go-to guy for a certain smiling, disarmingly puppy-dog-eyed malevolence. Free Willy aside, Madsen hasn’t really done much to shake off that typecasting: He’s appeared in numerous other movies that rely on that charming, slightly weary brutishness, from Donnie Brasco to Sin City to Tarantino’s Kill Bill and The Hateful Eight, which has unfortunately also meant spending a lot of time in the straight-to-video pile since the ’90s (and in 2012, the Celebrity Big Brother house). But no matter where he turns up, Madsen brings with him a reliable grit and admirable work ethic—even if, like the city that raised him, there’s a lot of overlooked soul beneath that hard-nosed surface. [Sean O’Neal]

13. Craig Robinson

Growing up on Chicago’s South Side, Craig Robinson took a lot of different jobs while he was still working out his distinctly smooth and musical comedy voice. That dedicated odd-jobbery reflects the early parts of his acting résumé, which is filled with forgettable-sounding roles like “Studio Guard #1,” “Security Guard #5,” or “Bouncer.” But Robinson has the great character actor’s knack for expanding his characters to fill all of the available space, something he proved often during his eight-year tenure on NBC’s The Office. As warehouse manager Darryl Philbin, the resident target for Michael Scott’s fumbling, childishly racist attempts to understand black culture, Robinson slowly rose in prominence on the show, rivaling John Krasinski and Jenna Fischer as one of its best irritated camera glancers. Robinson has since expanded into leading roles and drama, applying his usual aura of rock-solid calm to Morris From America and Mr. Robot. But he still has a talent for creating larger-than-life comedy characters out of smaller-than-average parts, something he proves with welcome regularity as Andy Samberg’s recurring criminal nemesis, “Pontiac Bandit” Doug Judy, on Fox’s Brooklyn Nine-Nine. [William Hughes]

14. Brian Doyle-Murray

It can’t be easy living in the shadow of your younger brother—particularly when that brother is Bill Murray. But while he hasn’t become a genre unto himself or been transformed into a living meme, Brian Doyle-Murray has earned his own rightful acclaim as a gruffer, slightly more crotchety version of their shared Chicago working-class earthiness. Like Bill, Brian came up through Second City and The National Lampoon Radio Hour before finding his way onto Saturday Night Live—the one with Howard Cosell, that is, followed by the more famous one where he co-anchored Weekend Update and earned three Emmy nominations for his writing. Doyle-Murray co-scripted Caddyshack and turned up in his brother’s movies like Scrooged and Groundhog Day, but he’s also been a reliable foil to other SNL players in movies like Modern Problems, National Lampoon’s Christmas Vacation, and Wayne’s World, while he’s brought a welcome, scabrous edge to sitcoms like Seinfeld, Get A Life, and The Middle. He can do drama, too (see his hangdog Jack Ruby in JFK), and he’s put that prickly burr of a voice to good use on dozens of cartoons like SpongeBob SquarePants and King Of The Hill. In fact, if you add up the myriad cultural contributions Doyle-Murray has made over the years—147 IMDB acting credits to Bill’s 83—statistically speaking, he’s the real breadwinner. [Sean O’Neal]

15. Terry Kinney

Steppenwolf co-founder Terry Kinney has now cornered the market on the older-but-wiser authority figure: somewhat world-weary, but inherently good at heart. See: McManus on Oz and his current gig on Good Behavior as parole officer Christian. But Kinney’s chameleon-like façade means that he’s shown up in everything from legal blockbuster efforts like The Firm and The Good Wife to period pieces like The House Of Mirth and The Last Of The Mohicans. He’s also made the most of his stage training, as there aren’t many actors who can so easily flip from the good to the bad side of the coin: He’s somehow as believable as a sadistic prison guard in Sleepers, a nerd in Fly Away Home, a sympathetic boyfriend in Thirtysomething, a badass in Billions, and a cop in FX’s Fargo. He told us that despite living in Brooklyn, he’s a Chicagoan at heart, which explains the Midwestern candor that translates in every role he plays. These days, he also has a busy career as a stage director, but when he shows up on screen, he makes the most of it, so that even something like The Mob Doctor gets a boost from his appearance. [Gwen Ihnat]

16. John C. Reilly

John C. Reilly’s Oscar-nominated role in 2002’s Chicago was something of a homecoming—at least nominally—for the actor who grew up in the movie’s namesake city. He stayed through college, attending DePaul, and like so many Chicago stalwarts, has roots in the Steppenwolf theater. Before starting in film, he appeared in its production of The Grapes Of Wrath in 1990 along with others on this list, including Gary Sinise and Jim True-Frost. Reilly, with his amiable, hangdog quality, has appeared in a remarkably versatile array of projects. He’s probably best known for his raucously funny work alongside Will Ferrell and Adam McKay in Talladega Nights: The Ballad Of Ricky Bobby and Step Brothers, but he’s been a player for Paul Thomas Anderson, Martin Scorsese, and Robert Altman. Reilly’s performances veer from the sad to the sweet to the unhinged. “Mr. Cellophane,” however, he is not, making an indelible impression on the movies he inhabits, most recently with a star turn in Kong: Skull Island. [Esther Zuckerman]

17. Gary Sinise

The Chicago character-actor tradition owes a lot to Gary Sinise. As the co-founder of the city’s famed Steppenwolf Theatre, Sinise helped create a veritable assembly line for Windy City Hey-It’s-That-Guys. Steppenwolf is also where Sinise refined his own famously intense gifts as an actor and director, gifts he first put on national display opposite John Malkovich in 1992’s Of Mice And Men. Since then, he’s carved out a distinctive niche for himself, occasionally as a leading man (as in the Philip K. Dick paranoia thriller Impostor, which used his manic, uneasy energy to good effect) but more often as the loose cannon that the hero—Nic Cage, Ben Affleck, or, more often than not, Tom Hanks—has to hold back from tearing some dickhead a new asshole. To be fair, Sinise seems much nicer in real life; instead of running screaming from the cultural ubiquity of his Forrest Gump character, he’s embraced it, with the Lt. Dan Band a fixture of USO tours and fundraisers for veteran groups. [William Hughes]

18. Gary Cole

There’s a creeping Midwestern evil to Bill Lumbergh, the soulless avatar of corporate corruption making Ron Livingston’s life hell in Mike Judge’s cult classic Office Space. Much of Lumbergh’s passive-aggressive faux friendliness—peppered with “Mmmmmmyeah”s and “That’d be great”s—comes straight out of Judge’s old Office Space cartoons, but it’s refined into a core of insincere loathsomeness by veteran Chicago actor Gary Cole. That false sincerity is key to Cole’s greatness, whether as a fake TV dad in The Brady Bunch Movie, a fake superhero on Harvey Birdman, Attorney At Law, or a fake cowboy politician on the last few seasons of The West Wing. Gifted with an irresistibly smarmy baritone, sharpened by his time at Steppenwolf and other Chicago-area theaters, Cole’s brilliance lies in letting just a hint of human dysfunction and panic sneak into his otherwise radio-perfect register. It’s no wonder he’s been such an easy addition to the world of incompetence-masked-as-confidence that makes up HBO’s Veep. [William Hughes]

19. Jim True-Frost

Jim True-Frost was born in Connecticut, but while attending Northwestern, he became a member of the Steppenwolf Theatre Company (like so many people on this list) as well as William Petersen’s Remains Theatre, racking up numerous Jeff Awards. Perhaps that’s why so many of his most memorable roles have involved being part of an ensemble, like in Singles, as well as acclaimed series like Treme and The Wire. As True-Frost has gotten older, he’s become adept at portraying wildly disparate historical figures, including F. Scott Fitzgerald’s famous editor Max Perkins in the Amazon series Z, Benjamin Franklin’s son William in a 2002 miniseries, and Eliot Ness on Boardwalk Empire. His aristocratic features and impressive stature allow him to travel seamlessly through any era—like this year’s Monsters Of God with Garret Dillahunt about the 1867 Comanche Wars—assuring him interesting character-actor roles likely for as long as he wants them. But what True-Frost always brings is a brave emotionality—from Prez’s attempts at teaching to Perkins’ befuddlement over how to deal with his most famous client—so that we can immediately relate to his characters whatever decade they happen to reside in. [Gwen Ihnat]