Few actors can take over an entire season of a television show quite like Bobby Cannavale. Between Boardwalk Empire and Mr. Robot, Cannavale has changed the stakes of several major drama shows with his villainous performances, earning the 2013 Emmy Award for Outstanding Supporting Actor in a Drama Series. While his television roles have been largely villainous, he's shown a much more versatile side to himself with his film roles.
Cannavale's cinematic filmography includes a good variety of comedies, dramas, and everything in between; he even had a short stint on the Marvel Cinematic Universe! While he's rarely granted a leading role, Cannavale is a reliable supporting player, bringing out the best in his co-stars. With a filmography far richer than anyone would expect, Cannavale has certainly made his mark on the silver screen.
10 'Fast Food Nation' (2006)
Richard Linklater's 2006 drama Fast Food Nation takes a Robert Altman-esque approach to the fast food industry and the insidious nature of livestock massacres and corporate greed. Cannavale gets to play the brief, menacing role of Mike, the manager of a meat packing plant who takes his anger out on innocent workers just fighting to earn their wages.
Mike trades his ability to transport children across the Mexican border for sexual favors from his female employees; Cannavale has played many villains before, but his Fast Food Nation character sadly reflects a corner of reality. Although brief, his character is among the most despicable in the story. Fast Food Nation is not among Richard Linklater's best movies, but an ensemble of fine performers mostly make up for the screenplay's lack of punch.
9 'Motherless Brooklyn' (2019)
Edward Norton's highly underrated 2019 crime drama period movie Motherless Brooklyn features a murderer's row of great character actors. Willem Dafoe, Alec Baldwin, Bruce Willis, Michael K. Williams, and Fisher Stevens all pop up within Detective Lionel Essrog's (Norton) adventure to unroot a conspiracy at the heart of New York City's public infrastructure development.
Cannavale appears as Tony Vermonte, a fellow detective serving alongside Essrog in service of the senior private eye Frank Minna (Willis). Cannavale helps make Frank's death at the beginning of the film even more emotionally overwhelming. It serves as Motherless Brooklyn's inciting incident and proves Cannavale's innate ability to pull focus even among a cast of seasoned pros.
8 'Win Win' (2011)
No one plays a disheveled dad quite like Cannavale. It's a role he's played countless times before, including in the Ant-Man films. However, Cannavale's performance as Terry Delfino in the 2011 sports comedy Win Win stands out as one of his more endearing parental characters. Delfino is the perfect presence of normality that helps make Mike Flaherty's (Paul Giamatti) hectic life seem even more convoluted in comparison.
While the film explores deeper themes about the importance of parental figures, Cannavale and Giamatti's comedic interactions create some of the lighter moments. Despite glowing reviews, the film flew under the radar and remains highly underappreciated despite having two of Giamatti and Cannavale's best performances.
7 'Blue Jasmine' (2013)
Cate Blanchett's work as Jasmine Francis in the 2013 dramedy Blue Jasmine is one of the best portrayals of neurosis and mental deterioration in recent memory. Although far from sympathetic, Jasmine is one of modern cinema's great tragic heroines, elevated by Blanchett's tour-de-force performance. Her sardonic, deluded nature stands compared to Chili (Cannavale), the boyfriend of Jasmine's sister Ginger (Sally Hawkins).
As a modern reinvention of A Streetcar Named Desire, Blue Jasmine casts Chilli as a much less reprehensible but equally brutish counterpart to Stanley Kowalski. His clashes with Jasmine provide much of Blue Jasmine's drama, even if his character is much less prominent to the story than Kowalski was to Streetcar. Cannavale more than holds his own against Blanchett, but the film remains squarely on Jasmine's POV as she sinks further into delusion.
6 'The Fundamentals Of Caring' (2016)
The Fundamentals of Caring revolves around the isolated teenager Trevor (Craig Roberts), whose livelihood is limited by his terminal illness. Trevor gets out of his comfort zone when he goes on a trip with his idiosyncratic caretaker, Ben Benjamin (Paul Rudd), to meet his father. Unfortunately, their journey only ends in disappointment when his dad, Cash (Cannavale), turns out to be nothing but a greedy, unsympathetic man with no interest in helping to raise his child.
Cannavale gets to play another "bad dad" in this underrated 2016 Netflix original. His role is uncredited and brief, but his intervention is pivotal for the story. Cannavale embraces the character's selfish persona without reducing him to a one-note villain, adding more depth to an already layered story.
5 'Chef' (2014)
Jon Favreau's 2014 independent dramedy Chef is more than just a celebration of great food. The film was Favreau's way of returning to his roots and focusing his efforts on making a personal, charming story about the importance of artistic integrity. Favreau gives a loveable performance as the chef Carl Casper, whose commitment to variety in his menu causes headaches for his manager, Riva (Dustin Hoffman).
Cannavale has a hilarious role as Carl's hapless sous-chef, Tony, who is simply caught up in the behind-the-scenes chaos that has engulfed the restaurant when Carl decides to spice up the menu. Aided by an impressive supporting cast, Canavalle and Fravreau inject Chef with enough warmth, humor, and goodwill to elevate an otherwise familiar story.
4 'The Irishman' (2019)
The same year that Cannavale popped up in Norton's Motherless Brooklyn, he also appeared in a much classier and significantly longer New York crime film. 2019's The Irishman follows Frank Sheeran's (Robert De Niro) career as a driver-turned-hitman working for the Bufalino crime family. The Philadelphia gangster Skinny Razor (Cannavale) is one of Sheeran's earliest employers in the mafia, and the lessons he learns in Philly with "Skinny" stick with him throughout his career.
Given his familiarity with the world of Martin Scorsese, thanks to Boardwalk Empire, Cannavale was a perfect fit for Scorsese's most personal crime film to date. Widely considered among the best Martin Scorsese movies, The Irishman is epic in length and scope, offering some of its impressive cast's most accomplished performances.
3 'I, Tonya' (2017)
I, Tonya's wild story of Olympic figure skater Tony Harding (Margot Robbie) might seem implausible if it wasn't based on real events. Craig Gillespie's darkly comedic 2017 biopic explores the wild facts of the case that emerged in the new media after Harding's arrest. Cannavale has an important role as Martin Maddox, a former reporter who covered Harding's case.
Like most characters in the film, Maddox breaks the fourth wall to recount the story's events directly to the audience. He serves as a hilarious yet level-headed narrator of the bizarre true crime story. Featuring one of Margot Robbie's best performances, I, Tonya is an acerbic, sobering look at one of the biggest scandals from the 90s, offering scathing criticism of the American sports industry.
2 'Danny Collins' (2015)
Cannavale has worked alongside many of the greatest actors of all time; 2015's Danny Collins paired him alongside the great Al Pacino. While Pacino's filmography within the 21st century hasn't quite rivaled his earlier work, Danny Collins gave him one of his best roles in years as an aging musician who tries to give back by reaching out to his son, Tom (Cannavale).
It's an uneasy relationship, and Cannavale shows that Tom is less than eager to forgive his father for being absent throughout the vast majority of his childhood. His scenes with Pacino are electrifying, with both actors portraying their character's emotions without succumbing to cheap melodrama. Danny Collins might not rank among Pacino's all-time best, but his earnest performance and dynamic with Cannavale elevate the film to exciting new heights.
1 'The Station Agent' (2003)
2003's The Station Agent is a delightful slice-of-life comedy that brings out Cannavale's most endearing qualities. The film focuses on the lonely model train hobby shop owner Finbar McBride (Peter Dinklage), who remains content not interacting with anyone else. Finabar's life changes significantly when the quirky snack shop owner Joe (Cannavale) sets up shop next to him. Jim's presence forces Finbar to come out of his shell and start being social for the first time in ages.
Cannavale's performance is wacky yet grounded and feels even more hilarious in comparison to Dinklage's grimness. The two actors form a richly compelling and endearing bond with the equally impressive Patricia Clarkson, creating a tender, bittersweet, and rewarding dynamic that makes The Station Agent a modern masterpiece of comedy and drama.