Before he was the two-time Academy Award-winning movie star, tequila mogul, philanthropist, father of twins, husband to Amal, and silver fox we all know and love, a young George Clooney was just another hopeful trying to make it in Hollywood. “I didn’t have a car so I rode a bicycle to auditions,” he told ET several years ago. “I was doing construction work for a living and I didn’t have any money at all.”

His first big break came in 1985, with a guest starring role on the TV series The Facts of Life, followed by a semi-regular role on Roseanne in 1988. He also appeared on an episode of The Golden Girls, played a detective on the show Body of Evidence, and grew his hair long to star as a rocker-motorycle-cop with an earring for a short-lived ABC drama called Sunset Beat.

But it wasn’t until the medical drama E.R., in which he donned scrubs and a close-crop haircut to play pediatrician Dr. Doug Ross, that Clooney finally became a household name. “It wasn’t just that it was an incredibly successful show, but it was a critically successful show,” he’s said. “To all of a sudden be getting Emmy nominations… I had never been in that category before. That was the turning point for my career, absolutely.”

What followed can only be described as a meteoric rise to mega stardom, with roles in acclaimed films such as The Perfect Storm, O Brother, Where Art Thou?, Syriana (his first Oscar win), Goodnight and Good Luck, Gravity, The Ides of March, the Oceans films, and many more. Along the way, he also nabbed two “Sexiest Man Alive” accolades from People magazine, founded a production company, sold his tequila company, got arrested for peaceably protesting, landed on the Time 100 list, became Julia Roberts’s bestie, joined the Council on Foreign Relations, won four Golden Globes, and—of course—got married to human rights attorney Amal Alamuddin in a glamorous, star-studded wedding ceremony in Venice, Italy.

And that’s just to name some of his accomplishments; just this year, Clooney also nabbed his first Tony nomination. “My biggest fear is doing the same things 10 years from now,” he’s said. “That would be a failure. It’s something you have to constantly reassess, and asking yourself what you are going to do next makes it a good, long, full journey.”

Here, a look at some photos of a young George Clooney on that journey.