The world is mourningMichael Madsen, an actor who blessed audiences with so many amazing performances. Some remember him as the foster father, Glen, inFree Willy; others remember him as Louise’s non-committal musician boyfriend, Jimmy, inThelma & Louise. Call him Michael “Midas” Madsen. Whatever he touched, it turned to gold. Unfortunately, the actor died of cardiac arrest at his home in Malibu, California, on June 20, 2025.
Madsen is also remembered for being one of directorQuentin Tarantino’s frequent collaborators, alongside other actors like Samuel L. Jackson, Harvey Keitel, Kurt Russell, Uma Thurman, and Zoë Bell. Whenever Tarantino called, the late actor always showed up. As a result, they ended up working together on five movies. All of their work together was good, but which is the best?
Here is how the Michael Madsen and Quentin Tarantino collaborations rank against each other.
5’The Hateful Eight' (2015)
The Hateful Eight
Events inThe Hateful Eightkick off in post-Civil War Wyoming. Jadedbounty hunter John “The Hangman” Ruth (Kurt Russell) is escorting fugitive Daisy Domergue (Jennifer Jason Leigh) to Red Rock for execution. Along the way, they begrudgingly pick up Major Marquis Warren (Samuel L. Jackson), a former Union soldier who also happens to be a bounty hunter with a fascinating tale to tell, and Chris Mannix (Walton Goggins), who says he is Red Rock’s new sheriff.When a blizzard strikes, they are forced to take shelter at Minnie’s Haberdashery, where they encounter nefarious figures.
Tarantino conceived it as a novel and sequel toDjango Unchainedbefore deciding to make it a standalone film. After the script leaked, he decided to abandon the production and publish it as a novel instead, before changing his mind again and making a movie.
Only Comes Alive in the Third Act
From Channing Tatum to Zoë Bell,The Hateful Eightoverflows with macho and femme power to please all fans. And if that’s not enough,Michael Madsen is drafted in to add layers to the secret scheming and off-beat violence quotientby a considerable factor. This stuck-in-location thriller from QT might not be his best work, but it remainsone of his cleverest and most entertaining pictures. Even better, it haswonderful cinematography, boasting an epic sweep. And nothing tops thatover-the-top climactic action sequence.
Unfortunately,the film is longer than necessary, with stretched moments of dialogue. Besides that, each character haslittle to no emotional depth. Perhaps Tarantino just didn’t know how best to change things after the script leaked. We forgive him.
4’Once Upon a Time…in Hollywood' (2019)
Once Upon a Time in Hollywood
It’s 1969 inOnce Upon a Time…in Hollywoodand times are changing.Former Western TV star Rick Dalton (Leonardo DiCaprio) is struggling to get work and so is his stuntman buddy Cliff Booth (Brad Pitt), who also has to deal with rumors that he killed his wife. Dalton, aware that young actress Sharon Tate and her director husband, Roman Polanski, live next door, tries to befriend them. Butthings take a dark turn when members of Charles Manson’s cult target these Hollywood figures.
Tarantino conceived the idea while working onDeath Proof. He was impressed upon learning that Kurt Russell had been working with the same stunt double, John Casino, for years.
Hardly the Best Hollywood Story
Pitt is dangerously goodas an optimistic stuntman in a film that pays homage to its Golden Age antecedents, as well as the headlines, via itsdark themes, era-appropriate costume design, and stylish aesthetic. You’ll love the scene where Rick gets to fight Bruce Lee. And as always, Tarantino gives usglorious views of feet. This time the feet belong to Margot Robbie. Who would say no?
However, it would be pretentious not to admit thatOnce Upon a Time…in Hollywoodis another disappointing pairing of Tarantino and Madsen, following their collaboration onThe Hateful Eight.The film is extremely overcrowded, resulting in little character development. From Timothy Olyphant to Al Pacino, there are too many stars, so someone like Madsen never gets to properly showcase his skills. He only appears briefly as a sheriff in the fictional western TV show,Bounty Law.
3’Kill Bill. Vol 1' (2003)
Kill Bill: Vol. 1
Kill Bill. Vol 1finds ‘The Bride’ (Uma Thurman), a former member of the Deadly Vipers Assassination Squad, preparing for her weddingat a chapel in El Paso, Texas. Unfortunately, members of The Deadly Vipers, led by her ex, Bill (David Carradine), attack the chapel. Wounded, The Bride informs Bill that he is the father of her unborn child, but he stillshoots her in the head. Luckily, she doesn’t die andonce she is fully recovered, she embarks on a revenge mission.
Quentin Tarantino and Uma Thurman came up with the Bride character during the production ofPulp Fiction. However, it would take several years for the director to write the script, beginning work in 2000 while living in New York City.
Bloody Mayhem
Kill Bill. Vol. 1should have been one of Michael Madsen’s proudest achievements yet, paradoxically, commentators rarely make any mention of it while discussing the actor’s extensive filmography, ignoring it for the second installment. The actor plays Bill’s brother, Budd, a former Vipers member, who now works as a strip club bouncer. Hebrings the required tough-guy aura, while stars like Thurman, Vivica Fox, and Lucy Liu also shine.
Tarantino also outdoes himself here. Hemakes good use of some of the classic martial arts and exploitation elementsand also treats audiences to a brief anime sequence. The only flaw?There’s little creativity in the plot. We’ve seen this story before.
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2’Kill Bill. Vol 2' (2004)
Kill Bill: Vol. 2
The Bride (Uma Thurman) continues her quest for revenge inKill Bill: Vol. 2. After defeating some of her targeted foes,she sets her eyes on Budd (Michael Madsen) and Elle Driver (Daryl Hannah). Budd proves to be quite capable, ambushing her and burying her alive, but she flees using knowledge imparted to her by Pai Mei (Gordon Liu). The chaos continues untilThe Bride confronts her former lover, Bill (David Carradine).
The film was produced together withKill Bill. Vol 1.Tarantino intended to make a single feature, but because the final product had a running time of over four hours, he was forced to split it into two.
Bill Finally Gets Killed
Tarantinosaved most of The Bride’s character development for the second installment, hence why it feels superior. There’s actually more of everything this time around.Madsen’s character gets greater room to play, and so does Bill, who appears physically for the first time.
Beyond that,the dialogue is richerinKill Bill: Vol. 2,with the philosophical chats between The Bride and Bill making for a great viewing experience. And if you are a martial arts fan, the training sequence with Pai Mei (Gordon Liu) will wow you because of the choreography and homage to kung fu cinema. Better yet, Tarantino blends in more genres, including spaghetti westerns andchanbara.
1’Reservoir Dogs' (1992)
Reservoir Dogs
Greatest everdirectorial debut? Quentin Tarantino’s first film,Reservoir Dogs,is abouta botched diamond heist orchestrated by crime boss Joe Cabot (Lawrence Tierney). The men for the job are six experienced robbers, all strangers to each other. Using color-coded aliases, they are Mr. White (Harvey Keitel), Mr. Orange (Tim Roth), Mr. Blonde (Michael Madsen), Mr. Blue (Edward Bunker), Mr. Brown (Tarantino), and Mr. Pink (Steve Buscemi). When the mission goes south, the survivors regroup at a warehouse, wherethey suspect that one of them is an undercover cop.
Tarantino planned to shoot the film with his friends on a budget of $30,000. Fortunes changed when Harvey Keitel was made aware of the script and agreed to come on board as a producer. Thanks to his presence, QT and his team raised $1.5 million.
The First of Many Great Collaborations
Whether it’s the robbers arguing about whether they should tip a waitress or them engaging in a Mexican standoff,Reservoir Dogsisn’t short of iconic moments. A movie like this would also be nothing without twists, and there are plenty of them. Someone in the group is indeed a cop, but you won’t easily tell who.
The violence is something to behold, too, and Quentin clearly knew what he was doing when he had the robbers wear white shirts. The red on their shirts is a constant reminder of how brutal a life in crime can be.Madsen oozes cool in his role as Vic Vega, even though he reportedly had difficulty filming the unnerving ear-cutting scene.
