Today, George Clooney is one of Hollywood’s biggest stars. But that wasn’t always the case. Clooney—the son of anchorman/television host Nick Clooney, and nephew of singer/actress Rosemary Clooney—spent years toiling in what he considered the semi-obscurity that was television in the 1980s and early 1990s. After playing handyman George Burnett for 17 episodes of The Facts of Life and Wellman Plastics foreman Booker Brooks on Roseanne, his big break came with the role of Dr. Doug Ross on ER. But even in the years since then, not every role has worked out for Clooney, as evidenced by these casting tales.

1. THELMA & LOUISE (1991)

Clooney auditioned multiple times for the part of J.D., but lost the role to Brad Pitt. Clooney was so upset about losing the part that he went out of his way to not see the movie. “The funniest thing is, I didn’t watch that movie for a long time,” Clooney remembered 20 years later at a Telluride Film Festival Q&A in 2011. “I was really stuck doing a lot of bad TV at that time. And I had auditioned and auditioned, and it got right down to Brad and I, and he got it. And I just couldn’t watch that movie for a couple of years.” When Clooney finally saw the film, he concluded that Pitt "was really good in it, and I would have f***ed it up somehow.”

2. RESERVOIR DOGS (1992)

Quentin Tarantino had specifically asked for Clooney to audition after seeing him in the straight-to-video film Red Surf (1989), in which Clooney played a drug dealing surfer. The actor admitted that he blew it, saying: “I didn’t get it because I gave a bad audition.” It couldn’t have been too terrible; in 1996, Clooney got the opportunity to star alongside Tarantino in From Dusk Till Dawn, from a script by Tarantino.

3. DRACULA (1992)

Clooney told Esquire that he auditioned for Francis Ford Coppola in the voice of a Kentucky hillbilly (he was born and raised in Kentucky): "This goddamn Dracula thing's comin' in here, comin' down this here slide and blowin' up like a ball-a-fire!” Coppola called Clooney’s agent and asked if there was something mentally wrong with him.

4. GUARDING TESS (1994)

Guarding Tess starred Shirley MacLaine as a former First Lady and Nicolas Cage as an exasperated Secret Service agent. Clooney remembered auditioning for the film as a humbling lesson when he spoke to The New York Times in 2002: “You can't help it sometimes. I was on ER and I was trying to not just do TV. For years, before ER, I was very successful in television. I was making $40,000 a week, and still I could not get an audition for two lines in a movie called Guarding Tess. All along, I had thought of myself as a film actor doing television, but at some point you have to face reality: I was a TV actor.”

5. JACK FROST (1998)

Originally, the plan was for Clooney to star as the titular musician who dies in a car crash on Christmas and comes back to life as a snowman. But Clooney and director Sam Raimi dropped out, and Michael Keaton and director Troy Miller stepped in. Clooney left so late in the process that there wasn’t enough time for the snowman’s head to be completely changed to resemble Keaton instead of Clooney. "Once it became Michael Keaton, we didn't change the head completely," one of the movie’s puppeteers and designated ‘performance coordinator’ explained. “We did some signature things to the chin and to the lips because Michael Keaton has this little mouth and talks out of the front of his mouth."

6. WILD WILD WEST (1999)

Clooney signed up to play Artemus Gordon in the Barry Sonnenfeld-directed film alongside Will Smith. Kevin Kline ended up playing Gordon in the critically-panned movie. Clooney was diplomatic in his official explanation for why he changed his mind. “We knew going into this that to make it work would be a stretch, but the opportunity to work with Will [Smith] and Barry [Sonnenfeld] was too exciting to pass up. Ultimately, we all decided that rather than damage this project trying to retrofit the role for me, it was better to step aside and let them get someone else.”

7. SIDEWAYS (2004)

Writer/director Alexander Payne (Election, About Schmidt) met Clooney when he was casting for Sideways, a movie which was destined to star Thomas Haden Church as Jack, the unsuccessful actor, and Paul Giamatti as the writer/wine connoisseur Miles. Clooney wanted to play Jack. Payne liked Clooney, but didn’t think anyone would believe that “the most handsome and successful movie actor is the most loser TV actor. I didn’t want that to be the joke.” Clooney recalled Payne telling him he was under serious consideration before never calling. In 2011, Payne cast Clooney in The Descendants.

8. A PRAIRIE HOME COMPANION (2006)

In Garrison Keillor’s introduction to the published screenplay, he wrote that Robert Altman (MASH, Gosford Park) opted for the public radio host and Lake Wobegon creator over Clooney. “I put in the announcer, pulling his pants on, trying to tell a story of how he got into radio and being interrupted by others. I wrote the part for George Clooney, who I thought was interested and who moviegoers would have enjoyed watching put his pants on, but Mr. Altman had let me know that he had cast me in the role.”

9. ARGO (2012)

Clooney ended up winning his second Oscar (the first was for Best Supporting Actor for 2005's Syriana) for producing 2013's Best Picture, but he had initially intended to star as CIA agent Tony Mendez, before scheduling conflicts with The Ides of March (2011) forced him to hand the project over to Ben Affleck. "I was doing Ides of March and gave [Argo] to Ben because we were ready to shoot," Clooney told the New York Post's Page Six.

10. THE MAN FROM U.N.C.L.E. (2015)

While director Steven Soderbergh was still involved with the film adaptation of the 1960s spy series, Clooney was forced to drop out because he needed back surgery. Guy Ritchie (Lock, Stock and Two Smoking Barrels, Snatch) ended up behind the camera.

11. BATMAN TRIUMPHANT

Because Batman & Robin (1997) was a critical and commercial failure, the intended next installment in the superhero series was canceled. Clooney had signed on for Triumphant; however, he said he approached Adam West (star of the original Batman TV series) at the 2015 New York Comic-Con and apologized for “ruining” Batman, and for the nipples on his Batsuit.