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Michael Block is a 14 time GLAM Award nominated writer, producer, and host of the podcast Block Talk. Throughout his time in the entertainment industry, he has worked on and off Broadway as a stage manager, written several produced plays, critiqued hundreds of theatrical performances, drag and cabaret shows, and has produced events randing from drag competitoons to variety concerts!
On Block Talk, he interviews nightlife personalities, covers the wide world of entertainment through features, ranking episodes, and recaps ALL of Drag Race, as well as Dragula and Survivor. He has interviewed hundreds of RuGirls that span the globe at DragCon NYC, DragCon LA, and DragCon UK.
In his free time, he makes one-of-a-kind jewelry and gift baskets with his mom. He is a proud member of the LGBTQ+ community.
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From Hollywood heartthrob to decorated thespian, Brad Pitt's long career has kept him among the industry's most beloved stars.From finding his way as a cowboy hitchhiker in Thelma & Louise to bringing audiences straight onto the racetrack in F1, Pitt's versatile resume reflects his ability to transform. And we're not just talking about that transformation in The Curious Case of Benjamin Button!
Though we all may have our favorite Pitt film of all time, they may not always align with the larger fandom. Thanks to apps like Letterboxd, we have a way to analyze our taste alongside other cinephiles. In terms of Pitt classics, the Letterboxd users have a very specific ranking regarding his best projects. These Pitt films currently stand out as the best of the best on Letterboxd. Are any of your favorites missing?
10 'Babylon' (2022)
Letterboxd Score: 3.9/5
Image via Paramount PicturesA film of grand proportions, Damien Chazelle's epic dramady Babylon is an homage to 1920s Hollywood that depicts the industry's transition from silent films to talkies. The sprawling period piece follows aspiring actress Nellie LaRoy (Margot Robbie) and fading movie star Jack Conrad (Pitt) as they navigate a world of extravagant parties, drugs, and the relentless churn of fame. Exploring themes of cinematic magic, exploitation, and the cost of dreams against the wild, decadent, and often brutal backdrop of Hollywood, Babylon brings the audience into the inherent tragedy of chasing fame that has otherwise been painted as a journey of intoxicating allure.
Babylon is a flawed masterpiece. Perhaps a bit bigger than it was ever intended to be, the film is excessive. With a giant cast of stars that also included Jean Smart, Diego Calva, Tobey Maguire, Olivia Wilde, and more, Pitt stood out among the pack as Jack Conrad. Unafraid to play in the sandbox of Hollywood-set films, Pitt eases into the role. He looks like a star, but he brings an edge of despair as a man losing his final hold on a career he longed to keep. Charming, affable, and terrifically horny, Pitt is the main appeal. The only problem is Pitt's Jack shares the spotlight with the equally engaging Robbie as Nellie and Luna as Manuel. Though he does have an essence of melancholy, a man grasping at the past, luckily for Pitt, it's not a reflection of his own fading career.
9 'Ocean's Eleven' (2001)
Letterboxd Score: 3.9/5
Image via Warner Bros.In 2001, Steven Soderbergh took a major gamble by rolling the dice with a remake of the 1960 Rat Pack film, Ocean's Eleven. A genuine ensemble film, the first installment of the trilogy follows friends Danny Ocean (George Clooney) and Rusty Ryan (Pitt) as they plan a heist of $160 million from casino owner Terry Benedict (Andy Garcia), the lover of Ocean's ex-wife, Tess (Julia Roberts). A genuine all-star masterpiece that kicked off the new millennium, Ocean's Eleven is a fast-paced film that is equally charming as it is thrilling.
A sharply and stylishly presented film with a cast you have to see to believe, Ocean's Eleven thrives thanks to its sensational performances, which also come from Matt Damon, Casey Affleck, and Elliott Gould. Meant to entertain with fun from start to finish, Ocean's Eleven may not offer much aside from seeing how the star-studded ensemble slips into their Rat Pack counterparts. For Pitt, he took on the role equivalent to Dean Martin's Sam Harmon. A cool, sharp-dressed associate, Pitt served as the right-hand man to Clooney's Ocean. He was an effortless charmer with natural charisma. Fans of the film may have noticed on multiple watches that Pitt's character seems to eat nonstop, noting that because Rusty was so busy, he had to eat whenever he had a chance. A film that helped define blockbusters in the 21st century, Ocean's Eleven would never have been the film it was without the dynamic chemistry between Clooney and Pitt.
8 'Moneyball' (2011)
Letterboxd Score: 3.9/5
Image via Sony Pictures ReleasingThe story that inspired Moneyball was not only a game-changer for baseball, but it also served as a game-changer for Pitt. The Bennett Miller-directed film followed the Oakland Athletics' 2002 season as their general manager, Billy Beane (Pitt), attempts to assemble a competitive team with a significantly smaller number of players compared to their rivals. Focusing on Beane and his deputy, Peter Brand (Jonah Hill), as they scouted the majors for undervalued talent using a sophisticated sabermetric approach that caused systemic shockwaves throughout the baseball community. Based on Michael Lewis' book of the same name, Moneyball took a niche subject and presented a sharp, touching portrayal of a monumental moment in baseball history.
Earning an Oscar nomination for his role, the film signified a shift for Pitt, who didn't have to play the heartthrob to be taken seriously. As Beane, Pitt hit a homer out of the park. Elevated to new heights by Hill's comic chops as they attempt to find common ground through their working relationship, Pitt's movie-star status evolved. His ability to play a good guy in a difficult spot exudes the typical Pitt you expect from him. Moneyball was a sports film that proved that behind-the-scenes stories are equally thrilling as those played on the field.
7 'The Assassination of Jesse James by the Coward Robert Ford' (2007)
Letterboxd Score: 4.0/5
Image via Warner Bros.Maybe, given our love for Westerns, it's worth giving The Assassination of Jesse James by the Coward Robert Ford a second look. Directed by Andrew Dominik, the epic revisionist Western is based on Ron Hansen's 1983 novel of the same name. The film follows the complex, obsessive, and ultimately fatal relationship between legendary outlaw Jesse James (Pitt) and his admirer-turned-killer, Robert Ford (Casey Affleck). Tackling the dark allure of our fascination with the anti-hero, The Assassination of Jesse James by the Coward Robert Ford explores themes of myth versus reality, fame, and betrayal during James' final months as a paranoid, legendary figure and Ford's desperate quest for notoriety, culminating in Ford's infamous assassination of James.
With a nearly three-hour runtime, the film is a sensational-looking visual that elevates the pair through an expertly crafted period drama that depicts an insightful moment in American mythology and lore. Perhaps not as daring as other Western dramas at the time, The Assassination of Jesse James by the Coward Robert Ford was still a Western masterpiece. By maintaining the character-driven story, Pitt and Affleck dive deep into their individual personas, encapsulating a different type of scarily captivating charisma. Perhaps an overlooked entry in Pitt's body of work, The Assassination of Jesse James by the Coward Robert Ford made you eager to see him in further Westerns. If you haven't seen the film yet, you'll also be given the gift of seeing the likes of Mary-Louise Parker, Jeremy Renner, Zooey Deschanel, and Sam Rockwell stretch their Western wares.
6 'Snatch' (2000)
Letterboxd Score: 4.0/5
Image via Sony Pictures ReleasingOnly Guy Ritchie can bring you a comedic crime thriller quite like Snatch. Containing two interconnected plots, Snatch follows the search for a stolen diamond as small-time boxing promoter Turkish (Jason Statham) becomes embroiled with a ruthless gangster, "Brick Top" Pulford (Alan Ford), who is willing to commit severe, sadistic acts of violence. With quirky criminals, a troublesome boxer with a thick accent, and a chaotic chase led by an inept team of robbers, Snatch is a thrilling, fast-paced comedy that masterfully weaves multiple storylines into one colliding adventure.
Energetic, sharp, and absurdly humorous, Ritchie's film is a laugh-out-loud gem. Though he may not have top billing, Pitt is a shining star in Snatch. He plays Mickey O'Neill, a bare-knuckle boxer who gets entangled in a scheme by his bookies. Now, is Pitt providing a perfectly solid and genuine accent? Not a chance, but he's still fantastic to watch. Even as handsome as he is, Pitt's ability to play and explore beyond the serious roles leading up to Snatch allowed him to tap into new sides of himself as a performer. A very different type of fight club, Pitt plays outlandish and over-the-top, rightly matching the tone of the film.
5 '12 Years a Slave' (2013)
Letterboxd Score: 4.2/5
Image via Searchlight PicturesPerhaps one of the most important films of the 21st century is Steve McQueen's epic historical drama, 12 Years a Slave. Based on the 1853 memoir by Solomon Northup, the film follows the freed mixed-race man, played by Chiwetel Ejiofor, after being kidnapped from Washington, D.C. by two conmen in 1841 and sold into slavery. Put to work on plantations in Louisiana for 12 years before his release, the unflinching film serves as a powerful account of the horrors of American slavery, detailing the slave trade, the dehumanization of enslaved people, and one man's resilience in maintaining hope and his identity.
Telling the harrowing stories of slavery in America can come with a world of difficulty. Balancing authenticity without romanticizing the dark stain on the nation's history can result in an inauthentic film. Thankfully, director McQueen's take on Northup's story was so well executed that it was met with universal acclaim. For his part, Pitt played Samuel Bass, a Canadian abolitionist carpenter who shows Solomon kindness by helping him get word to his friends. Representing a rare voice of decency and a brief beacon of hope, Pitt's Bass was a moral anchor for the film, though the small but crucial part was met with some pushback for feeling out of place in the overall narrative of the film. Pitt also served as a producer on the project.
4 'Thelma & Louise' (1991)
Letterboxd Score: 4.2/5
Image via MGM-Pathé CommunicationsThough it may not have been his first film, Thelma & Louise was the movie that put Pitt on the Hollywood map. Directed by Ridley Scott, Thelma & Louise is a buddy comedy-drama that follows two close friends, unhappy housewife Thelma (Geena Davis) and strong-willed waitress Louise (Susan Sarandon), who go on a weekend fishing trip that turns into a flight from the law after Louise shoots a man attempting to rape Thelma at a bar. They become fugitives, heading for Mexico in a '66 Thunderbird, discovering freedom and a new strength in their bond as they evade a nationwide manhunt, transforming from mundane lives into self-realized women. A pinnacle of 90s cinema, the film will forever be remembered by that car and that cliff.
Though the film was very much focused on the aspirational friendship between Davis and Sarandon's titular characters, the movie got steamy when they picked up a hitchhiker, J.D. (Pitt). From the jump, it was clear that Pitt was born to be a star. The utter charm he exuded when he knocked on the car, of course, Thelma couldn't deny his advances! J.D. was more than just a drifter needing a ride; he was a representation of something new. The moment he took his shirt off in the hotel room, it was evident that Pitt was destined to be the ultimate heartbreaking boy-next-door bad boy. Over the years, the role has followed Pitt around simply for its iconic status. It's also haunted his friends, like Clooney, who lost the part to Pitt.
3 'Fight Club' (1999)
Letterboxd Score: 4.3/5
Image via 20th Century StudiosThe first rule of fight club is don't talk about fight club. Unless we're talking about one of the most influential films in the history of cinema. Directed by David Fincher, the film follows Edward Norton as an unnamed narrator who suffers from insomnia and is discontented with his office job. He joins an underground bare-knuckle "fight club" with soap salesman Tyler Durden (Pitt) to combat alienation and consumerism. The club escalates into chaos through the anti-establishment movement Project Mayhem, while the narrator becomes entangled with an impoverished but beguiling woman, Marla Singer (Helena Bonham Carter). Ending with one of the greatest twists in the history of movies, Fight Club has maintained a top spot in many cinephiles' favorite lists.
In the '90s, Pitt's range of roles was always layered in charisma and sex appeal. To close out the century, Pitt ended on a high note thanks to his phenomenal performance as Tyler Durden. Pairing extraordinarily well with Norton, serving as his enigmatic foil-slash-actual identity, Pitt's charisma lured audiences in, engaging them with the mysterious, rough-around-the-edges character. Is there a universe in which Pitt could have earned himself an Oscar nod for his role? Absolutely, yes. Fight Club is Pitt's definitive '90s movie.
2 'Inglourious Basterds' (2009)
Letterboxd Score: 4.4/5
There are actors known for being frequent collaborators with the same directors. Brad Pitt was not necessarily that person. Instead, he's had the pleasure of working with a range of the best and brightest in the business. By the time Quentin Tarantino got his hands on Pitt for their first project, he was ready to drop him into the black comedy war thriller, Inglourious Basterds. A twist in history, the film follows two converging plots to assassinate Nazi Germany's leadership at a Paris cinema. In story one, a team of Jewish-American soldiers called "The Basterds," led by Lieutenant Aldo Raine (Pitt), who scalps Nazis, engages in a British operation. The other, Shosanna Dreyfus (Mélanie Laurent), a Jewish cinema owner whose family was killed by SS Colonel Hans Landa, plans her own fiery revenge at a propaganda film premiere attended by Hitler. Pitted against the fearsome SS colonel Hans Landa (Christoph Waltz), these storylines intertwine, culminating in a violent showdown where film, vengeance, and historical revisionism collide to bring down the Third Reich's leaders.
Revisionist history and Tarantino at his finest, Inglourious Basterds was a genre-blending thrill ride that pushes you to reexamine everything you think you know about World War II. Though the fictionalized, entertaining version of the war offers an exciting journey, it is crucial to separate truth from reality to understand the necessity of playing into the alternate reality. Perhaps the reason we continue to have a very similar moniker attached to Pitt in the films on this list is that no one does charm quite like him. Lieutenant Raine was an excellent role for Pitt, who went all-in on the Tarantino universe. Violent and unrestrained, it's those moments he flaces that signature smile that has you instantly taken.
1 'Se7en' (1995)
Letterboxd Score: 4.4/5
Image via New Line CinemaThanks to Fincher's Se7en, if we ever get a mysterious box, be fearful of its contents. The film follows two homicide detectives, William Somerset, a jaded veteran (Morgan Freeman), and David Mills, an eager rookie (Pitt), hunting a sadistic serial killer who bases his killings on the Seven Deadly Sins. A killer who hopes to leave a lasting impression through his commentary on society, it’s that shocking finale that completely took the audience's breath away. A terrific film noir thriller, Se7en was a trendsetter in cinema.
Still riding the wave as a sought-after young Hollywood actor, Pitt took on a slightly different part in Detective Mills. Working alongside two powerhouse performers, Freeman and Kevin Spacey, Pitt's performance was elevated to ensure he wasn't clichéd in his role. By showing a bit of a serious side, Pitt changed how audiences viewed him. At the time, his performance seemed mixed, but looking back at the film and his performance, Se7en continues to prove that he's always had that dramatic edge. Of course, the ending was anything but glorious for Mills, who fell straight into the killer's trap. "What's in the box?" Don't ask a question you don't want the answer to!
Se7en
Release Date September 22, 1995
Runtime 127 minutes
Writers Andrew Kevin Walker
English (US) ·