Following its premiere at the 82nd Venice International Film Festival, where it was nominated for the Golden Lion, and a limited run in theaters, Jay Kelly makes its global debut today on Netflix. Directed by Noah Baumbach from a screenplay he co-wrote with Emily Mortimer, the film features an ensemble cast, led by George Clooney. Throughout his career, Clooney has established himself as one of the industry’s best actors and is one of the few who is a throwback to the old Hollywood charisma of the past. In many ways, he feels like a throwback, and yet he has found ways to also feel remarkably fresh across a series of fine performances that have showcased his various talents. As he earns solid reviews for his turn in Jay Kelly playing, no stretch here, a famous actor, this felt like the best time to look back at his five best performances ever!

Honorable Mention: Three Kings (1999) as Major Archie Gates

At the time that Three Kings was released, Clooney was establishing himself as a movie star and hitting his stride following the debacle of 1997’s Batman & Robin. In 1998, he starred in Out of Sight, which played directly into his charisma, but 1999’s Three Kings subverted his movie star image and allowed him to play someone a bit more rough around the edges. Written and directed by David O. Russell from a story by John Ridley, Three Kings is set following the end of the First Gulf War and focuses on the uprisings against Saddam Hussein in 1991.

Despite the serious-sounding premise, Three Kings is actually a black comedy that derives humor but a particularly serious situation, and Clooney is completely on board as Major Archie Gates, delivering his lines with a grizzled dry wit that makes the character completely memorable. In addition to this, there is nuance to the performance, and Clooney takes the audience on a journey as his character goes from someone with completely selfish intentions (getting the gold) to finding a bigger purpose by protecting Iraqi civilians and prisoners. Over time, the film and Clooney’s participation in it have become more known for the tense disagreements between the actor and O. Russell, with legend saying that the latter didn’t want Clooney for the role. Whether that’s the case or not, Clooney ended up being perfectly cast, and it proved to be a pivotal role to show his growth as an actor on the big screen.

5. Ocean’s Eleven (2001) as Danny Ocean

Clooney is known for his old Hollywood charisma, and no film showcased it better than 2001’s Ocean’s Eleven. Directed by Steven Soderbergh from a screenplay by Ted Griffin, Ocean’s Eleven is a remake of the 1960 Rat Pack film and follows Danny Ocean (Clooney) and his friend Rusty Ryan (Brad Pitt) as they assemble a crew to plan a heist of $160 million from a casino owner named Terry Benedict (Andy Garcia), who happens to be the lover of Ocean’s ex-wife Tess (Julia Roberts). Ocean’s Eleven is the perfect example of a Hollywood film, complete with an all-star cast, that is both entertaining and made with style and substance. Clooney hits in perfectly here and exudes cool confidence as Danny Ocean.

Whether he’s planning his big job with his crew or reuniting with Roberts’ Tess, Clooney becomes the definition of a movie star. His screen presence feels effortless, and he displays a suave self-assuredness that, while not trying too hard, has continued to make this one of his signature roles. He carried this natural charm throughout the sequels, but Ocean’s Eleven remains the best example of Clooney’s cool demeanor and class in a role that fits the actor like a glove.

4. Out of Sight (1998) as Jack Foley

In a role that feels like a precursor to his role in Ocean’s Eleven, Out of Sight, at the time, felt like Clooney’s true coming-out party as a big-screen movie star. While he had appeared in films before this, following his stint in television on ER, the actor hadn’t had a role that truly played to his strengths, and Out of Sight did just that. Directed by Steven Soderbergh from a screenplay by Scott Frank, Out of Sight is adapted from Elmore Leonard’s 1996 novel and follows career bank robber Jack Foley (Clooney), who breaks out of jail to pull off one last job, only to become entangled with a U.S. Marshall named Karen Sisco (Jennifer Lopez), which becomes extremely romantic and particularly complicated.

Out of Sight is Clooney’s arrival as a leading man, as it plays to his natural screen presence and charisma. Jack Foley might be a criminal, but Clooney makes him likable enough that you hope that not only does he pull off this last job, but that he also complicates the career of the girl and ends up with her in the end. Much of the spice that comes from Out of Sight is the combustible chemistry between Clooney and Lopez, particularly in a scene where they meet at a hotel bar as their dialogue is intercut between their discussion and love scene.

This is definitely how you sell chemistry. Not just having two good-looking actors on screen, but also having grade A performers sparring with each other with ease. The movie was a big moment for both actors, and that’s like why they both rose to the occasion. While Out of Sight wasn’t a huge hit upon release, the film did its job of proving that Clooney was meant to lead future projects and that his time as a true movie star was finally coming to fruition.

3. O Brother, Where Art Thou? (2000) as Ulysses Everett McGill

Proving that he didn’t have to just rely on his natural charm, Clooney decided to go a bit offbeat in O Brother, Where Art Thou?, proving that his talents went beyond his old Hollywood screen presence. Written and directed by Joel and Ethan Coen, O Brother, Where Art Thou? is loosely based on Homer’s The Odyssey and follows three escaped convicts in rural Mississippi who are searching for hidden treasure in the summer of 1937 while being pursued by a very determined sheriff.

O Brother, Where Are Thou? is deliberately quirky, and Clooney matches pitch perfectly as a character who believes he’s the smartest guy in the room, where that couldn’t be further from the truth. Reportedly, Joel Coen gave Clooney precise direction on how the character should be played, and once the actor found that groove, he had no issue embracing being ridiculous and also diving into some physical comedy. While Clooney didn’t sing himself in the film during his performance of “Man of Constant Sorrow” (that credit goes to Dan Tyminski), he also shows commitment to that musical performance, making it one of the film’s standout moments.

Clooney got to cover all the gamut of performance here, making the character equal parts pompous but also a lovable fool that made Ulysses a bit endearing. If anything, O Brother, Where Art Thou? showcased that Clooney had much more range than just playing to his good looks and suave charisma, even though he was still able to use it, but by turning it on its head to give a fun, memorable, and offbeat performance.

2. Syriana (2005) as Bob Barnes

Clooney won his only acting Oscar for Best Supporting Actor for his turn as Bob Barnes in Syriana, and it’s because it proved to be his most transformative work. Written and directed by Stephen Gaghan, Syriana is loosely based on Robert Baer’s 2003 memoir See No Evil and is a politically charged thriller focusing on the oil industry and the people personally involved in it.

Clooney went all in portraying Bob Barnes, a CIA agent who is feeling the weight and complexity of his job. The actor famously gained 35 pounds for the role and aged his appearance, but his commitment went beyond his physical transformation. The actor was able to convey the inner turmoil of someone who has been beaten down by his job and the experiences that have come along with it. It’s a performance that could’ve been very loud and showy, but Clooney is completely understated, showcasing the necessary emotional depth and desperation of Bob Barnes’ predicament throughout the film. He drops all notions of heroism and movie-star charm to portray a character grounded in a harsh reality that stands as some of his best dramatic work to date.

1. Up in the Air (2009) as Ryan Bingham

Clooney’s performance in Up in the Air stands as a personal best for me because he’s able to play into his charms but with humanity and a sense of vulnerability. Ryan Bingham, at first, seems like a role that Clooney has showcased several times before, until his true fears are revealed and he begins to wear his emotional depth on his sleeve. Directed by Jason Reitman from a screenplay he co-wrote with Sheldon Turner, Up in the Air is based on Walter Kim’s 2001 novel and follows Ryan Bingham (Clooney), a suave traveling corporate downsizer who is very good at his job and has a desire to reach ten million frequent flyer miles.

However, his whole routine is upended upon the arrival of the ambitious Natalie Keener, a 23-year-old who believes that all the travel is unnecessary and that firing can be done over a video conference. As the story moves along, it becomes clear that Ryan is particularly lonely and empty as his nomadic life has prevented him from truly living. Clooney proves here that he’s keenly aware of his persona and realizes that the true surprise will be to turn it on its head and surprise audiences with a performance that goes beyond his screen presence and digs at something deeper. This is a character that wears an exterior of confidence but is secretly deeply insecure, and Clooney conveys these nuances masterfully as he peels the layers away from Ryan to make him a fully formed character with depth.

This is aided by his different forms of chemistry with his female co-stars. His at-odds connection with Kendrick that eventually turns into a genuine bond works on a non-romantic level, while his chemistry with Vera Farmiga, who portrays a frequently traveling businesswoman and potential love interest, bursts with the right of attraction as this man, who is deeply afraid of commitment, breaks down his walls and begins to open his heart. Up in the Air proves to be a great vehicle for all of Clooney’s talents as a charismatic movie star, but also as one hell of an actor.

Jay Kelly is now streaming on Netflix.

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