What do you get for the man who has everything? Unfortunately, we're not besties with Leo Dicaprio (yet) and don't need to dwell on that good problem. Because shopping for cool 40th birthday gifts is out of the question, we took on the only task available to us: ranking every year of existence for a living legend whose life has been more than semi-charmed since before he could legally drink. This is the guy who had (probably) the best celebrity profile of all time written about him and his epically titled entourage when he was just 24.
And yet it would be disingenuous to say that Leo peaked in '98. The Prince of the City turned god of the game has more or less been coasting on the highest wave since he froze to death for love, with a borderline airtight résumé his fellow Hollywood heartthrobs would kill for—his worst years are your best dream. The voting body of the Academy Awards have, once again, failed to duly recognize greatness, but that's what we're here for.
Salute on turning the big four-oh, Leo. In honor of the beginning of what can potentially be a better, richer Clooney Phase™ than Clooney himself enjoyed, Complex has ranked every year of Leo's life, from "broke-up-with-my-latest-model-girlfriend" worst to "I'm-king-of-the-world" best.