Before we begin, let’s remember that virtually every young actor in Hollywood was discussed at some point to play Anakin Skywalker in the Star Wars prequels. Before landing on relative newcomer Hayden Christensen, George Lucas considered hundreds of actors, from unknowns to A-listers and everyone in-between. So if you were a young white guy working in the industry in 2000 and weren’t up for the role, you were probably doing something wrong.

That said, there is something irresistible about the “what could have been?” of these casting calls, especially when they include some of the biggest stars alive. And Leonardo DiCaprio sparked our curiosity, just a little bit, by discussing with Shortlist the meeting he had with Lucas about playing Anakin, way back when. Like the role of Robin in Batman & Robin, DiCaprio says, “I don’t think I was ready for anything like that.” He continued, “[I] just didn’t feel ready to take that dive. At that point.”

Looking back at DiCaprio’s post-Titanic years, it’s impressive—and maybe even a little miraculous—how carefully he threaded that needle of sudden stardom. Sure, The Man in the Iron Mask and The Beach were duds, and the doomed Don’s Plum remains an odd anomaly on his IMDb page. But then he emerged again in 2002 with Gangs of New York as the Leo we know today—friend of A-list directors, actor willing to challenge himself at every turn, an aspiring equal to the likes of Daniel Day-Lewis. Gangs of New York opened the same year as Attack of the Clones. The choice DiCaprio made, with 20/20 hindsight, of course, seems pretty obvious.

Although, given recent rumors about Anakin Skywalker potentially showing up in Star Wars: The Force Awakens, DiCaprio may have also missed his chance to show up, once again, in one of the biggest movies of all time. Probably a trade-off he can live with.