John-John, we hardly knew ye at 40... or 50

Had it not been for talk show host Oprah Winfrey, this milestone would have otherwise slipped past the unobservant of us: John F. Kennedy, son of the newly elected 35th President of the United States, was born 50 years ago today in Washington, D.C. Fate in the form of a small-plane crash on July 16, 1999 deprived us of a fortysomething and fiftysomething John-John.

Given that her talk show would compete against parade coverage and an onslaught on National Football League (NFL) games on Thanksgiving day, Oprah threw down her best weapon against the competition's programing by broadcasting her interview with Kennedy that aired on September 3, 1996. Oprah embodied the reaction of any red-blooded female seated next to Kennedy: She was starstruck, smitten and careful not to offend People magazine's 1988 selection as "The Sexiest Man Alive." Nobody would dare piss off the young man whom the media dubbed "America's prince" -- and risk future opportunities to schmooze with John-John in Manhattan. Or DC. Or The Cape.

Rich and astonishingly handsome, Kennedy could have gone wrong as a spoiled little rich boy or an aristocratic Charlie Sheen: substance abuse, hookers, criminal arrests, multiple arrests. Credit Jacqueline Bouvier Kennedy Onassis for raising a daughter and son who neither conveyed a sense of obvious entitlement nor lost their sense of proportion, humanity and humility.

Kennedy attended Brown University where he majored in history. Although he aspired to pursue an acting career, Kennedy reportedly earned a law degree from New York University to appease his mother. He required three attempts to pass the New York state bar exam; one failure generated the headline "Hunk flunks" from one of Gotham's tabloids. Kennedy worked as an assistant district attorney in New York City for four years, and then switched gears like he might the bicycle that he rode through the streets of Manhattan. In October 1995, Kennedy launched political magazine George, which sported the tagline "not just politics as usual." While George allowed Kennedy the luxury of playing on the political stage -- albeit, in the back, back stage -- without running for office, Kennedy was not above taking risks.

In August 1997, Kennedy penned an editor's letter that took two of his cousins -- aspiring Massachusetts gubernatorial candidate Joseph P. Kennedy and his brother Michael Kennedy -- to task for sexual indiscretions that ultimately ended their political careers. Kennedy violated the family omerta by publicly admonishing others with whom he shared a sacred bloodline. "Two members of my family chased an idealized alternative to their life," he wrote. "One left behind an embittered wife, and another, in what looked to be a hedge against mortality, fell in love with youth and surrendered his judgment in the process. Both became poster boys for bad behavior."

Kennedy's well-documented personal life included dalliances with actresses Daryl Hannah and Sarah Jessica Parker, model Ashley Richardson, pop diva Madonna. In September 1996, he married Carolyn Bessette, a publicist at Calvin Klein, in a secret ceremony at a wood-frame chapel in the First African Baptist Church in Cumberland Island, GA.

A quintessential New Yorker, Kennedy rooted for the New York Mets and -- like Spike Lee, Woody Allen and the Baldwin brothers -- sat court side at New York Knicks games. Images of Kennedy riding through the Manhattan on a bike with his suit pant leg hiked up or on Rollerblades was as iconic as New York as a taxicab or a "bagel with a schmear". While he had a cameo role on Murphy Brown, Kennedy is probably best known for his non-appearance in the 1992 Seinfeld episode "The Contest" as the object of Elaine's lust and the first intimate partner of Marla the virgin.

We'll never know if Kennedy would pursue a career in politics and would run for the U.S. Senate heat once held by his uncle, Robert F. Kennedy Jr. -- to succeed Daniel Patrick Moynihan in 2000 or Hillary Rodham Clinton in 2008. It doesn't take Magic 8-ball to predict that Kennedy would have grown more damned handsome and distinguished in his 40s and 50s.

A shout-out to Oprah for giving us food for thought on The Coolest "Sexiest Man Alive." In the 25 years since People first bestowed the honor upon a misleadingly kinder and gentler Mel Gibson, Kennedy remains the only non-actor upon whom the title has been bestowed.