Inside The Complicated Life Of John F. Kennedy Jr.

John F. Kennedy Jr. was famous from almost literally the moment he was born. His father had just been elected one of the youngest presidents in United States history, and the country fell in love. His parents loved him, too. Doug Wead, author of "All the President's Children," told ABC News that father and son were extremely close. "There was a bond between the two of them. John was definitely the apple of his eye," he said.

JFK Jr.'s life, however, was marked by tragedy; his father would not live to see his third birthday. As he grew older, Kennedy would struggle to find his place in the world. He was a socialite and a lawyer, a tabloid fixture and a political servant. He had a number of high-profile celebrity relationships just as he bristled against his public image as a famous hunk, but then he settled into a marriage in secret to avoid the attention. He reportedly had quite a temper in private, but those who knew him also remember him as a people-pleaser who could command a room. Bartender Joe Diggs recalled (via Esquire), "John looked in your soul and he understood it. John was one of the nicest people I've ever met. I don't know anybody who said anything else but that about that man. I just don't."

In other words, Kennedy's life was a complicated one. Read on for a look back at the all-too-brief life of one of the most famous children in America.

The coverage of John F. Kennedy's administration often focused on the young president's family, including his beautiful wife Jackie and his children. After JFK's eventual assassination, Jackie cemented that narrative in history when she quoted her late husband's favorite musical to a journalist from Life Magazine (via People). "Don't let it be forgot, that for one brief, shining moment there was Camelot," she said, conjuring images of JFK as King Arthur, presiding over a beautiful kingdom.

The term was applied retroactively, but the fawning press attention was there throughout those first few years of John F. Kennedy Jr.'s life. Photographers captured him playing underneath his father's desk as he worked in the White House, and the press even reported that the family called the president's son "John-John." That nickname followed JFK Jr. for the rest of his life, but he reportedly disliked it. According to Kathy McKeon, the family's nanny, it wasn't even something they called him. "John hated the nickname and no one in the family called him that," she wrote in her memoir "Jackie's Girl: My Life with the Kennedy Family." "It came about when a White House reported had once overheard the president call out to his toddler son twice in quick succession."

It's perhaps the most visible example of a theme that would continue throughout JFK Jr.'s life: the difference between his public and private life. No matter what people thought they knew, there's always more to learn.

Even after his father's death, John F. Kennedy Jr. remained a public figure. When it came time to attend college, he chose to apply to Brown rather than Harvard (as his father had done), likely to set himself apart from his family legacy. Still, documents unearthed decades later and published in Page Six (via W) showed his mother Jackie Kennedy's involvement in his application. In fact, she wrote his application herself. "My son is in Africa," the former First Lady wrote. "I will attempt to fill this out for him." When JFK Jr. ran into academic trouble during his freshman year, his mother wrote a letter to the dean about her son's efforts to fix his grades. "I look forward to hearing he is off probation — and to never getting another notice that he is on it," she wrote.

At Brown, John was heavily involved in theater. His classmate and fellow actor Rick Moody wrote about his talent in the Brown Alumni Magazine, recalling, "John showed up ready to act, and when the time came he delivered his lines with brio, with uncanny reserves of charisma. What's the surprise in this? He'd been acting his entire life. One performance after another."

Though he pursued law rather than acting, he appeared in a play called "Winners," in New York in 1985. As The Irish Echo noted, the play was eerily about three people who drown, foreshadowing the tragedy waiting in JFK Jr.'s own future.

In the 1990s, John F. Kennedy Jr. would launch a magazine devoted to the intersection of politics and pop culture; more on that below. He should know; JFK Jr. lived at that intersection through a series of high-profile relationships with celebrities. His father reportedly had a fling with Marilyn Monroe, but JFK Jr. set his sights on her eighties equivalent: Madonna. According to InStyle, biographer J. Randy Taraborrelli wrote that the Material Girl was frightened of Kennedy's temper. She even called him "slightly more frightening" than her ex Sean Penn. The relationship didn't last long.

In the early 90s, Kennedy went on a few dates with Sarah Jessica Parker. She resented the attention they got, telling The New York Times (via InStyle), "He's a nice man, but for God's sake, I feel like I should apologize for dating him. It has become the defining factor in the person I am. It's pathetic." She even called the whole endeavor "the Kennedy fiasco." This relationship didn't last long, either.

In the late 80s and early 90s, Kennedy courted "Splash" star Daryl Hannah. While the attractive duo made for a picture-perfect couple whenever they stepped out together, things were more complicated behind the scenes. "John just found Daryl so self-absorbed," Kennedy”s friend and biographer Steven M. Gillon told InStyle. They ultimately went their separate ways after Kennedy was insulted by Hannah's insistence on talking about her dog while his mother was sick.

One of the first things that comes to mind when many people hear the Kennedy name is the family's significant number of high-profile tragedies. In John F. Kennedy Jr.'s case, his childhood was shaped by the assassinations of his father and uncle. Biographer J. Randy Taraborrelli told Good Morning America, "You can't really imagine what it would do to a young person to have both his father and his uncle murdered in the same way."

By many accounts, Kennedy tried to live as normal a life as possible — except when it wasn't possible. Richard Wiese, a Brown classmate, reflected, "[He] liked to be treated like everyone else and he didn't mind being the butt of a joke. In some respects, I found the most remarkable thing about John was how relatively normal he was despite his fame." This was something Kennedy himself thought about. "It's hard for me to talk about a legacy or a mystique. It's my family," he once said (via The Tampa Bay Times). "The fact that there have been difficulties and hardships, or obstacles, makes us closer."

One of Kennedy's attempts to seem normal was his insistence on riding his bike to work. "Don't you just love the image of John Kennedy Jr. on his bicycle, free as a bird," writer Michael Gross recalled to ABC News. "This is a beautiful image of someone who lives in a cage, finding a way to escape."

After several years as an Assistant District Attorney, John F. Kennedy Jr. left his post. A representative of DA Robert Morgenthau's office confirmed his departure to The Orlando Sentinel, and the outlet had no further information about what Kennedy planned to do next. A role in government? Back to school to study something else?

By September 1995, the world had its answer. He'd decided to launch a magazine called George, a glossy that would merge the worlds of pop culture and politics. Its first cover famously depicted supermodel Cindy Crawford dressed as the magazine's namesake, George Washington. At the press conference where he unveiled the launch of the magazine, JFK Jr. acknowledged that having a marquee name like his own on the masthead would hopefully benefit things. "Certainly it helps, and it draws attention, and what any new launch needs is that. But ultimately, this magazine is going to stand or fall on whether or not it's a good magazine," he insisted (via WABC).

Right out the gate, the magazine was a hit, thanks in part to its charismatic founder. However, it was not without controversy. David Pecker — who would later go on to quash negative stories in the National Enquirer on behalf of Donald Trump — described accidentally by the magazine as "a living, breathing orgasm." According to Esquire, one pundit even called the magazine a "net loss of information." His involvement in the magazine would soon cause trouble in JFK Jr.'s life.

While John F. Kennedy and Carolyn Bessette-Kennedy's wedding may have seemed idyllic, their marriage was anything but. According to a close friend who spoke with Edward Klein in the biography, "The Kennedy Curse: Why Tragedy Has Haunted America's First Family for 150 Years," Bessette quickly withdrew after the nuptials, crumbling under the spotlight. "She didn't want to go out," the friend said. "She would ditch John's friends, not show up for dinner, refuse to go to people's houses or events. She burned a lot of bridges."

It seems that Bessette fixated on the long hours her new husband was spending at his magazine. She would fax him to come home, according to Klein. When he did return to their apartment, he would find her doing drugs. A George staffer spent a night out with Bessette and witnessed her taking multiple trips to the bathroom, coming back with powder on her nose. "The next morning, John came into the office and asked, 'Why did you keep my wife out so late?'" the staffer recalled. "And I said, 'A better question, John, is why your wife didn't want to go home.'" Their arguments reportedly became violent, with JFK Jr.'s friends convinced Bessette was responsible when he severed a nerve in his wrist.

Eventually, Bessette's meddling led to the departure of Kennedy's partner Michael Berman from George. The magazine was in danger of failing when Kennedy complained to a friend, "It's impossible to talk to Carolyn about anything. We've become like total strangers." It was July 1999.

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