Great Actors Who Call Chicago Home Part 3

Practicing social distancing and staying in our Chicago homes means we are glued to our favorite streaming services more than ever before. If there was ever a time to catch up on movies you have missed or revisit personal favorites, now is the ideal time to do so. When it comes to actors on the small and big screen, you don’t have to scroll through your Netflix or Prime queue for very long to find performers who have called the Windy City home. Today we continue our spotlight on famous actors who got their start in Chicago before becoming fan favorites the world over.

Vince Vaughn: Funnyman Vince Vaughn has a certain swagger and comedic timing that has made audiences rollover from laughter for the past two decades. Although born in Minnesota in 1970, Vaughn grew up in suburban Buffalo Grove. He then moved to Lake Forest, where he graduated from Lake Forest High School in 1988. That same year he was cast in a car commercial and decided to head to Hollywood to pursue acting. After appearing in a few TV shows and after school specials, Vaughn got his first movie role in the film Rudy, where he met longtime collaborator Jon Favreau. The two worked together in 1996’s independent hit comedy Swingers, where the tall and funny Vaughn really shined in the eyes of audiences. Roles in films like The Lost World: Jurassic Park and The Cell beefed up his resume, and in 2003 his starring turn in the comedy Old School lifted Vaughn to leading man status. This was followed by a string of colossal comedy hits, including Starsky & Hutch, Wedding Crashers, The Break-Up, and Couples Retreat. The native of the Chicago suburbs expanded his talents of late in season 2 of HBO’s True Detective and Brawl in Cell Block 99.

John C. Reilly: John C. Reilly has carved out an amazing career lending his multifaceted talents to some the best film of the past quarter-century. The actor was born in 1965 and raised in the Chicago Lawn neighborhood. He is an alumnus of the Theater School at DePaul University. Reilly got his start in supporting roles in such films as Casualties of War, Days of Thunder, and Hoffa before really coming to the attention of audiences in the hit Boogie Nights. From there, the Chicago native appeared in three of the Oscar-nominated films for Best Picture in the year 2002: The Hours, Gangs of New York, and Chicago. A character actor beloved by directors like Martin Scorsese and Paul Thomas Anderson, Reilly was able to make the successful jump to more comedic fare thanks to his ability to bring the perfect mix of nuance and subversiveness to his roles. Comedies like Step Brothers, Talladega Nights: The Ballad of Ricky Bobby, and the animated Wreck-It Ralph brought a whole new audience to appreciate the actor’s talent. Whether a role calls for sincerity or all-out hilarity, John C. Reilly has proved that time and time again, he is one of Chicago’s best exports to make it big in Hollywood.

John Cusack: The well-known Chicago actor has starred in roles that have defined generations throughout his career. Born in Evanston in 1966, Cusack graduated from Evanston Township High School in 1984. Cusack first caught audiences’ eye in Sixteen Candles, followed by a starring role in Rob Reiner’s The Sure Thing in 1985. The actor’s performances in Say Anything…, Gross Point Blank (for which he co-wrote the screenplay), and Eight Men Out, showed that the Evanston native had real staying power in Hollywood. Cusack continued to star in fan favorites across all genres, including the action-packed Con Air, the mind-bending Being John Malkovich, and the Windy City rom-com High Fidelity. Despite his success in Hollywood, Cusack spends most of his time in Chicago and currently has a condo located on the Gold Coast.

That’s it for today’s list of great Chicago actors, but we are not done. Tune in next week for more performers from the Windy City who have gone on to star in some of our favorite films. 

ERIC KAPLAN AND DEAN’S TEAM CHICAGO