While his visual flourishes as a director are highly appreciated, Quentin Tarantino is most renowned for his writing. His snappy dialogue has its own unmistakable style, his nonlinear narratives revolutionized the way stories are told on the big screen, and his characters are surprisingly humanized takes on pulp archetypes.

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Tarantino usually casts the perfect actors to play these roles – he can never go wrong giving a part to Samuel L. Jackson, Christoph Waltz, or Uma Thurman – but they’re not always the notorious filmmaker’s first choice.

Django Freeman In Django Unchained

Perfectly Cast: Jamie Foxx

Jamie Foxx at the end of Django Unchained

The role of slave-turned-bounty hunter Django Freeman in Tarantino’s spaghetti western hit Django Unchained was a difficult one to cast. The actor needs plenty of dramatic chops to capture the harrowing historical context, but also comedic abilities and leading-man charms to handle the heart, humor, and heroism of the story.

Jamie Foxx, both a widely adored standup comedian and an Oscar-winning dramatic actor from his work in Ray, was the perfect choice to bring this character to life.

Almost Cast: Will Smith

Will Smith riding a horse in Wild Wild West

While Foxx ended up being the perfect choice to play Django, Tarantino actually wrote the part with a different actor in mind: Will Smith. Smith has been one of the biggest movie stars in the world since the ‘90s, and has used that time to show off his versatility as an actor.

Smith likely would’ve made a great Django, but according to IndieWire, he turned it down because of how Tarantino’s script approached the story: “I didn’t want to make a slavery film about vengeance.”

Vincent Vega In Pulp Fiction

Perfectly Cast: John Travolta

Vincent looks in the briefcase in Pulp Fiction

After starring in hit movies like Grease and Saturday Night Fever throughout the ‘70s, John Travolta’s career fell into a slump throughout the ‘80s. The role of Vincent Vega in 1994’s Pulp Fiction gave the actor a much-needed (and much-deserved) career comeback.

Travolta nailed deadpan line deliveries like, “Oh, man, I shot Marvin in the face,” and in the Jack Rabbit Slim’s sequence, audiences were thrilled to see him back on the dancefloor.

Almost Cast: Michael Madsen

Budd in his boss' office in Kill Bill

It’s impossible to imagine anybody besides Travolta playing Vincent, but according to IndieWire, Tarantino actually wrote the part for Michael Madsen. However, Madsen had committed to appearing in Wyatt Earp before the offer for Pulp Fiction came through.

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When Travolta was cast, Vincent became the brother of Madsen’s Reservoir Dogs character Mr. Blonde – real name Vic Vega – and Tarantino planned a Vega Brothers spin-off that never came to fruition.

Mr. Blonde In Reservoir Dogs

Perfectly Cast: Michael Madsen

Mr Blonde tortures a cop in Reservoir Dogs

Tarantino got his filmmaking career off to a spectacular start with Reservoir Dogs, whose nonlinear storytelling, homage-driven style, and idiosyncratic dialogue both made the director a superstar and revitalized American indie cinema.

Part of the movie’s hard-boiled charm is that it has no straightforward heroes (except for the undercover cop in the robbers’ midst), but the ear-slicing Mr. Blonde is easily the most sadistic of the bunch. Michael Madsen played this role to perfection, bringing an unnerving charisma to his sociopathic antics.

Almost Cast: George Clooney

Seth Gecko holding a gun in From Dusk Til Dawn

While Reservoir Dogs was originally planned as a lo-fi $30,000 indie movie, the budget ballooned over $1 million when Harvey Keitel agreed to star as Mr. White and signed on as an executive producer.

According to Digital Spy, George Clooney read for the role of Mr. Blonde. Tarantino turned him down, but later gave him the lead role (opposite himself) in Robert Rodriguez’s vampire-infested crime caper From Dusk Till Dawn.

Cliff Booth In Once Upon A Time In Hollywood

Perfectly Cast: Brad Pitt

Brad Pitt on Spahn Ranch in Once Upon a Time in Hollywood

The fact that Once Upon a Time in Hollywood revolves around an actor and his stunt double presented an interesting casting challenge, because the two leads needed to share tangible chemistry as best friends and also had to bear a resemblance to each other.

Brad Pitt doesn’t actually look an awful lot like Leonardo DiCaprio, but the duo’s on-screen brotherly love was convincing enough to sell the dynamic. Pitt went on to win an Oscar for his charming portrayal of one of the deadliest men in the world.

Almost Cast: Tom Cruise

Tom Cruise using a pay phone in American Made

According to /Film, Tarantino decided to cast the lead roles of Once Upon a Time in Hollywood in pairs, because the chemistry had to be just right. DiCaprio and Pitt were always the top choices, but Q.T. had a few backups in case one or both of them were unavailable or they didn’t respond to the material.

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Tarantino explained, “I had maybe eight different pairings of actors that could go together.” One of the actors he met with was Tom Cruise, which makes sense for Cliff because Cruise is a literal stuntman. Tarantino didn’t reveal who he would’ve paired Cruise with.

Col. Hans Landa In Inglourious Basterds

Perfectly Cast: Christoph Waltz

Christoph Waltz at the premiere in Inglourious Basterds

Christoph Waltz won his first Academy Award for Best Supporting Actor for playing the sadistic S.S. Colonel Hans Landa in Inglourious Basterds. He convincingly played Landa’s friendly facade, which made the revelation of his true sinister nature even more unsettling.

Waltz is arguably the second most adept actor at delivering Tarantino’s unique dialogue after the undisputed champ, Samuel L. Jackson.

Almost Cast: Leonardo DiCaprio

Leonardo DiCaprio holding a hammer in Django Unchained

According to MTV, Tarantino originally wrote Landa with Leonardo DiCaprio in mind. However, after completing the script and beginning pre-production, he realized the part should be played by a native German-speaking actor.

During the ensuing casting process, Tarantino began to worry that he’d written an unplayable role – and then the perfect actor waltzed into the room. DiCaprio would later play the sadistic villain in Tarantino’s next movie, Django Unchained, instead.

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