Winning an Oscar is the dream of almost every actor, actress, and precious stage dog—we love you, Uggie!—this side of Hollywood and Vine. What aspiring thespian hasn’t clutched a hairbrush while standing in the mirror, tearfully thanking her agent, parents, and Pilates instructor who knew the name of that discreet plastic surgeon? But what they don’t tell you when you step off the bus from Iowa—because that still happens, right?—is that winning an Academy Award can also be a curse. Or you just have a really bad knack for picking scripts. (We’ll go with cursed.)

Hard to believe it has been fifteen years since we watched sports agent Jerry Maguire flip out and start a whole new life and career with the world’s most precocious kid by his side. The stars of this film have continued to impress audiences, and have had some pretty significant things happen in their personal lives as well – just like Jerry. Come take a look at where these stars are now.