Illustration by Mark Stamaty

Prince, Michael Jackson and Madonna. One last name, three big birthdays. The big 5-0. Mike crossed the threshold on August 29. Madonna hit it on August 16, and Prince is the elder of the bunch, having turned 50 on June 7.

Fifty? How did that happen?

To some, 50 is a marvelous milestone; to some it's a time to re-evaluate; to others, it's the beginning of the end. When we see our icons turn 50, we can't help but wonder…which one is it for them? Unlike the millions, the mansions and the fame—turning 50 is something we all can relate to.

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Aging, the great equalizer.

But, of course, puzzling over this trifecta of pop royalty dashing over the hill is less about them, really, than it is about us. When one has vivid memories of junior high or high school make-out sessions to "Darling Nikki" and all of sudden Prince is 50, it is only natural to think: "How the hell old am I?" When you can pull out old photographs of you dressed up like Madonna at a seventh grade Halloween Party, and now Madonna is older than your mom was when she took you to that party, it hits you: "Jeez, I'm really getting up there."

But there is comfort in this realization of immortality. As pop stars age, something about them seems more accessible. They are suddenly more like us. Celebrities that we thought had perfect lives and perfect bodies are now…well, a little troubled and wrinkly (or so altered by surgery that they are a little scary). And we love it!

Fifty is an age that, for most people, sparks careful reflection on the successes and failures in their lives. Could this really be so different for the ultra-famous?

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Take Madonna. She must look at her 50th birthday with pride at the fact that she is still making it rain on performers half her age. Forget Beyonce. With a new hit tour, Madonna is the still baddest chick in the game.

Transfer that thought to our own lives: We may not have a sold-out tour. But in giving props to the "Material Girl," we can take a moment to look at ourselves and think, "I did good." Reflecting on a life well-lived is a great feeling whether you're a pop star on stage or a mom fixing Pop-tarts in your kitchen.

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And what about Prince? As one of the most talented musicians of our time, he is still heralded as royalty and with age he has become sophisticated and mature and, in many ways, more fabulous. His concerts are still the hottest tickets in town, and he has successfully transitioned from the "big freak" of the '80s to the biggest talent of the 20th century.

Like many of us, he must stop sometimes and think, "Boy, I was a little wild in my younger days, but boy did I have a blast." And like the rest of us, he probably feels lucky that he made it through in one piece and is happy for the person he's become.

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At 50, it's a good time to look back at our youthful indiscretions and get a hearty chuckle out of them. The hair that made our parents crazy, the drugs, the wild behavior that almost got us sent to a military academy.

Character-builders, we call those experiences now, challenges and great memories. And hey, Prince's early days make most of ours look about as wild as our great-aunt's Mah Jong game. But like Prince, we can turn out alright, maybe even get better with age.

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Then there's Michael Jackson. Poor thing. He represents the less joyful side of turning 50. That point where we all look up and say, "What the hell happened?" One day we're riding high and the next we look up and everything is in the crapper. Kids gone bad, career gone wrong. At 35, there was resilience; at 50, hopelessness creeps in and sometimes stays.

Michael Jackson represents the part of us that thinks: Could this happen to us? Could we live the life of our dreams and then one day, we're being pitied by the world? If the most famous man in the world can crumble like this, what hope is there for us mere mortals?

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Plenty. That's the good thing about gauging ourselves against Michael. It's easy to look at him and feel like we could never possibly be that weird or screwed up. Our lives may be drama-filled, but M.J. serves as a cautionary tale to us all. Take a fifty-and-fabulous approach to aging and never let your life turn into a "Thriller."

Like Madonna and Prince and Michael, we all approach 50 from different places. Whether we are pleased to be 50, lucky to be 50 or sad and confused to be 50, if none of them have faded from the scene, then we don't have to either.

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So let's raise a glass to salute the icons of our youth as they celebrate 50 this year. And let's raise a glass to all the regular Joes who have traveled these last decades with them, through the good, the bad and the ugly. (Did you hear that History album?—sheesh)

Now is a great time to reflect on not only what these artists have meant to our lives and our culture, but also a time to reflect on just how far we all have come…and how far we all have yet to go.

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Jam Donaldson is a writer, attorney and television producer based in Washington, D.C.