Best & Worst: George Clooney

Best: Fail Safe (2000)

Based on the Cold War novel by Eugene Burdick and Harvey Wheeler, Fail Safe reunited Clooney with his ER co-star Noah Wyle, alongside the likes of Richard Dreyfuss and Harvey Keitel.

A TV movie broadcast on CBS, it earned massive plaudits for breathing new life into the material, proving it was just as timely and excruciating as it ever was. With his Hollywood looks and easy charm, Clooney is pitch perfect as Colonel Jack Grady, making Fail Safe one of his finest achievements.

Worst: Leatherheads (2008)

Clooney’s third time behind the camera (after Confessions Of A Dangerous Mind and Good Night, And Good Luck ) is sadly a stumble for the burgeoning director. Though he manages to assemble a stellar cast – Renée Zellweger, Jonathan Pryce, John Krasinski – the film feels flatter than a deflated football.

Not that Clooney isn’t trying. The period detail is great, and the director’s obviously got a passion for the subject matter. Sadly, that passion doesn’t translate to the big screen.

Best: Good Night, And Good Luck (2005)

Clooney’s sophomore directing gig is far more successful - a really classy black-and-white offering.

Also scripted by the silver fox, the film follows the clash between veteran journo Edward R. Murrow (David Strathairn) and U.S. Senator Joseph McCarthy. Stepping in to play the co-producer of show See It Now , Clooney proves adept at directing himself – something that not many actor-turned-directors pull off.

Worst: The Good German (2006)

You’d think pairing up with the inimitable Cate Blanchett was a fail safe move, right? Sadly, you couldn’t be more wrong.

Clooney plays American journalist Jake Geismar, who attempts to solve a mystery in a post-war Berlin even as he attempts to track down his mistress. With Steven Soderbergh at the helm, this looked like a surefire hit. Sadly, the director’s more interested in the period detail than he is in developing decent characters. Poor Cloon.

Best: Three Kings (1999)

Clooney famously locked horns with director David O. Russell on the set of this sandy war drama, but that doesn’t really matter when the resultant film is as top notch as Three Kings . The Cloon buddies up with Mark Wahlberg and Ice Cube for a post-Persian War satire in which a gold heist takes place after the Iraqi uprising against Saddam Hussein.

Critic Roger Ebert praised it as a “weird masterpiece, a screw-loose war picture that sends action and humour crashing head-on into each other and spinning off into political anger”.

Worst: One Fine Day (1996)

Capitalising on his ER heartthrob image, Clooney finds himself in romcom terrain – which, in Hollywood, means he's dangerously close to what they call 'selling out'.

You can see why he was tempted, mind. The opportunity to roll around in the hay with Michelle Pfeiffer was, of course, a particularly alluring one. And though the two Hollywood heavyweights (nowadays, anyway) strike a few sparks, there’s little to love about this formulaic romance.

Best: Fantastic Mr Fox (2009)

He may be your typical swaggering American, but even Clooney goes weak at the knees when it comes to the storytelling of Roald Dahl. Here he gets to play one of the coolest Dahl characters ever – the titular Mr Fox, who rallies against mean farmers who want to rid their land of wildlife.

It’s to Clooney’s credit that his silky tones are never lost in the animated hilarity. Our favourite smooth operator turns Mr Fox into one seriously cool dude. You guessed it, it's fantastic.

Worst: The Perfect Storm (2000)

Perfect storm, maybe. Perfect movie? Far from it. While director Wolfgang Petersen creates gob-smacking CGI vistas as a Bermuda hurricane goes mental at sea, Clooney and co get drowned in all the special effects. Oh the humanity.

The plot, such as it is, has Clooney setting off on a desperate fishing trip (along with crew Mark Wahlberg and John C. Reilly), only to face whopping 100 ft waves. Other than that, there’s no discernable drama to be found here.

Best: Out Of Sight (1998)

Before J-Lo became cinema’s version of a highway pile-up (ugh, Monster-In-Law ), Clooney proved that the popstress could do good on the big screen if paired with the right sort of talent.

Together, Clooney and Lopez share crackling chemistry. He’s a career bank robber who’s cracked out of a Florida prison. She’s a US Marshal. Together they share a car boot (as you do), then she spends the rest of the film trying to track him down. Sexy stuff and a top grade crime thriller.

Worst: Spy Kids 3D Game Over (2003)

Just one of the many mind-boggling cameos contained in the third Spy Kids movie, you suspect that the likes of Clooney and Elijah Wood were only roped in after being bribed by director Robert Rodriguez.

Clooney’s cameo is perhaps the briefest, as he crops us as the villainous Devlin – a role he was also suckered into playing in the first Spy Kids . George, do you never learn?!

Best: Up In The Air (2009)

Clooney’s cosying up to the ladies again, here hopping into the sack with the frankly gorgeous Vera Farmiga. He’s a corporate downsizer, and spends his time jetting from one corner of America to another in order to fire people on a company’s behalf.

It’s one of Clooney’s finest ever big screen performances. Naturally, he nails the slick, besuited part of the character, but then blushes in surprising amounts of emotional depth – not least in that teeth-kicking scene on his lover’s doorstep. Talk about crushing a man’s heart with your heel.

Worst: Batman & Robin (1997)

Ah, the big one. The poo icing on the turd cupcake. The disastrous fourquel responsible for destroying many burgeoning film careers (Chris O’Donnell and Alicia Silverstone are still to recover) is, miraculously, now little more than a curiously awful blip on Clooney’s CV.

So terrible that you have to open the window to air the room afterwards, Joel Schumacher’s maudlin, infantile attempt at keeping the Batman franchise ticking over is now the poster boy for how not to do a comic book movie. And Clooney’s Batman is forever remembered as the one who has nipples on his batsuit. Oh the shame.

Best: Michael Clayton (2007)

Lauded as one of the sharpest films of the year, Michael Clayton has smarts and style by the briefcase load. It was so good, in fact, that Entertainment Weekly called it “better than good, it just about restores your faith”.

Clooney is the titular Clayton, a D.A who ‘fixes’ problems for a New York law firm. Except then things start going wrong, as the survival of the company belonging to litigator Karen Crowder (Tilda Swinton) hangs on the outcome of a multi-billion-dollar settlement overseen by Clayton’s friend and lawyer Arthur Edens (Tom Wilkinson). Trust us, it doesn’t get much classier than this.

Worst: The Harvest (1993)

He’s a tramp, but you love him. Clooney dresses up as a transvestite in this little-seen thriller. He landed the role because his cousin Miguel Ferrer was the lead. Wonder what Ferrer’s up to these days…

Not only did The Harvest have Clooney wearing lipstick and belly-bearing tops, but it gave him the fantastic character name 'Lip Syncing Transvestite'. This is just two years away from the actor's big break with ER – if only he’d waited a little bit longer…

Best: Oceans Eleven (2001)

The one responsible for catapulting Clooney into A league super-stardom. Sure, he had charisma on the small screen as Dr Ross, but would The Cloon be able to charm quite as well on a cinema canvas? You bet he could – especially with a little help from his friends.

Contributing to a sparkly cast that included Brad Pitt, Don Cheadle, Matt Damon and Julia Roberts, Clooney’s still the one your eye drifts to as he masterminds an epic casino heist. If anybody could replace Frank Sinatra in this remake, it was him.

Worst: Oceans Twelve (2004)

Another swing and a miss for Steven Soderbergh, as the director brings back almost the entire cast of the first Ocean’s – including, naturally, Clooney – but fails to recapture the vital zing that made that glitzy heist caper so captivating.

This time around, Clooney and co are robbing for their lives when the owner of the casino they duped in the first Ocean’s tells them he’ll have them killed unless they pull off a job for him. Though it’s great to see the gang back together, Ocean’s Twelve suffers from the curse of sequelitis – it’s lazy and far too full of itself.

Best: Burn After Reading (2008)

Clooney does funny, and pulls it off with aplomb. He’s also responsible for the film’s knee-jerk “Oh my God!” moment (see above), which is as hilarious as it is horrific.

Directed by the Coen Brothers, Burn After Reading has Clooney playing a Treasury Department employee and U.S. Marshal who has a gift with the ladies. Clooney proves once and for all he can do funny – and well. Is there anything this man can’t do?

Worst: Welcome To Collinwood (2002)

Before Burn After Reading , Clooney tripped over comedy in this heist flick loosely based on Italian caper I Soliti Ignoti . Sadly, the resultant movie is only sporadically funny, hampered by duff dialogue and leaden storytelling.

The Cloon plays Jerzy, a wheelchair-bound safe cracker, as Sam Rockwell’s Pero decides that he’d be far more attractive to Jennifer Esposito if he just had a little more cash.

Best: The Thin Red Line (1998)

Everybody knows director Terence Malick likes to take his time, and the director finally made his big screen comeback after 20 years with The Thin Red Line . Frankly, it was worth the wait. Though by no means perfect, the film contains the kind of intensity that is rarely seen on the big screen.

Clooney closes the film with a killer speech. As a commanding officer, he takes over the C Company and delivers a warm but sceptical oration that really drives Malick’s point home. Hard-hitting stuff.

Worst: Return Of The Killer Tomatoes! (1988)

An inauspicious debut, Clooney clearly wasn’t wielding quite the same Hollywood heft he’d acquire later in life, here signing his image away for a pulpy atrocity that doesn’t even work as a crummy B-horror.

Currently a mightily impressive 0% fresh on Rotten Tomatoes, there’s obviously no love for this attempt at resurrecting the Killer Tomatoes brand. We’d tell you the plotline, but we’re pretty sure nobody actually cares…

Best: The Ides Of March (2011)

Clooney’s back in the hot seat – that’s the one the director normally sits in – calling the shots on this political thriller. Proving he’s every bit an actor’s director, Clooney gets the very best out of Ryan Gosling, who plays a press secretary dragged into a political scandal.

Worst: The Peacemaker (1997)

Clooney has a go at being James Bond, but discovers it’s not as easy as just sipping alcoholic beverages and sleeping with the pretty ladies.

Here he’s playing U.S. intelligence officer Lt. Col. Tom Devoe, who teams up with Dr. Julia Kelly (Nicole Kidman) to track down some Russian military officers who’ve pinched weapons to sell to terrorists. Those pesky Russians. Though Peacemaker makes a good crack at being an American Bond, the ingredients just don’t gel.

Best: O Brother, Where Art Thou? (2000)

Clooney's first tango with the Coen Brothers gave him an early hit with this offbeat, hilarious caper.

Josh Winning has worn a lot of hats over the years. Contributing Editor at Total Film, writer for SFX, and senior film writer at the Radio Times. Josh has also penned a novel about mysteries and monsters, is the co-host of a movie podcast, and has a library of pretty phenomenal stories from visiting some of the biggest TV and film sets in the world. He would also like you to know that he "lives for cat videos..." Don't we all, Josh. Don't we all.