The JFK Jr. We Loved: Close Friends Look Back at the (Ridiculously) Handsome but Down-To-Earth First Son

His image "was this 'John John' cartoon," says former Grateful Dead lyricist John Perry Barlow. "It was not him at all"

Editor’s note: This PEOPLE cover story was originally published on Aug. 1, 2016. Tuesday marked the 20th anniversary since the death of the former first son known simply as JFK Jr.

When the small plane John F. Kennedy Jr. was piloting plunged into the Atlantic on July 16, 1999, killing him at age 38 along with his wife, Carolyn Bessette Kennedy, 33, and her sister, Lauren Bessette, 34, the world mourned yet another tragedy in a family that often seemed cursed. His friends mourned something more: the loss of a man who was warmer, funnier and far more complex than the public knew.

His image “was this ‘John John’ cartoon,” says former Grateful Dead lyricist John Perry Barlow. “It was not him at all.”

Hoping to set the record straight, some of his closest confidants participated in a TV documentary, I Am JFK Jr., and opened up to PEOPLE.

“When you watch the film, you can’t help but think, ‘What if?'” says its director, Derik Murray. John’s friends wonder that too, but mostly they value the many ways he enriched their lives.

“It’s nice to remember how great he was,” says financier Chris Oberbeck, a former housemate, “and to share it.”

John F. Kennedy Jr. plays in the Oval Office while father John F. Kennedy works. Courtesy JFK Library

HIS FATHER’S SON

John told me, “One thing I remember — that’s not just something impressed on me by my mother or the photos — is my father used to hide candy in his desk in the Oval Office, and I would crawl around in there looking for it.”

—former Clinton aide and CNN contributor Paul Begala

John brought his father’s leather chair from the Oval Office to our fraternity house. Sometimes he’d swivel around and joke about who he’d have in his [future] Administration. He’d say, “Oberbeck, you might be an aide” — and then he’d start laughing. He had this thing of who would be where in his administration — it was a running joke.

—Chris Oberbeck

His father’s assassination colors everything. One day I was walking with John and my son, who was then 3, and I said, “He’s exactly the same age you were when your father was killed.” And John said, “You never get over it.”

—Andover classmate Sasha Chermayeff

Ron Galella/WireImage

A RELUCTANT HUNK

Anything about him being a sex symbol made him so uncomfortable. I remember I was interviewing for an assistant to be my backup. I told John, “You should meet the girls too,” and he said, “Every time they walk in here, they look like they’re going to throw up. It’s too embarrassing! You make the decision.”

—PR strategist RoseMarie Terenzio, John’s longtime assistant

He came to our Austin office around 1996, and he wanted to fax something. He asked for a hand, and this woman looks up and there’s John F. Kennedy Jr. in her file room. I kid you not, she hyperventilated. People had to come help her.

—Paul Begala

A MAN OF THE PEOPLE …

John took the subway all the time. If someone came up to him, he would often say hello, there was no irritation.

—Brian Steel, former assistant district attorney, now CNBC executive vice president

… WITH FRIENDS IN HIGH PLACES

He had a flirtation with Madonna — they saw each other a few times. She teased him and she was irreverent, and he liked it. Then it kind of faded, but they stayed friendly.

—a friend

I was working in the White House when the Monica Lewinsky scandal was going on. I had a fax machine, which very few people had the number to. It starts kicking in, and there’s no cover sheet, just a page — it was John. It just said, “Dear Mr. President, I sat under that desk — there’s barely room for a 3-year-old, much less a 21-year-old intern. Cheers, J.K.” Typical John. I showed the President, and he laughed his butt off.

—Paul Begala

BRAINS AND BRAWN — BUT NO COORDINATION

I think he was slightly misunderstood because he was such a sweetheart — people think anybody that’s been through so much and they’re still this happy-go-lucky person must be kind of a dummy. The one thing I would want is for people to see that John was a really serious, hard-hitting thinker who would have done great things.

—Sasha Chermayeff

People need to know what kind of fabulous man he was. I was his housemate [in college], and yes, he was messy, yes, he was a little bit of a klutz, but it was a joy living with him. People would come, we would have dinner, discuss politics, everything from nuclear disarmament to civil rights.

—Christiane Amanpour

John was fast and strong. He worked out a lot — he was a good worker-outer. He was really good at Frisbee … but in football? He was no [Hall of Fame receiver] Lynn Swann.

—Brian Steel

From left: John F. Kennedy Jr. and Carolyn Bessette Kennedy in 1999. Justin Ide/Getty

JOHN AND CAROLYN

He was enchanted with her — body and soul — from the minute he met her [in 1994]. He struggled with her inability to cope with the public nature of their life. But he never wavered in his commitment to helping her.

—Brian Steel

They had a really intense passion that manifested in loving each other but also in unbelievable fights. I don’t think it was an easy relationship. You’ve got this electricity and this magnetic attraction that was so powerful. It certainly wasn’t boring.

—Chris Oberbeck

In that last year of his life, there was some distance emotionally that hadn’t been there before. When you’re no longer blinded by the beauty and the love and the lust, when you start to feel like you’re really getting to know the person, it gets intense. He had a really intense period of questioning whether or not they could make their marriage work. Children, no children, maybe he was ready, maybe she wasn’t. She was a very complex woman, but they were deeply connected. What was going to happen, we’ll never know.

—Sasha Chermayeff

EYE ON THE PRESIDENCY?

Once we were in a meeting with Sen. Al D’Amato, who said John should run for mayor of New York City. After we left, I asked him, “Would you ever run for mayor?” and he said no. I asked him why, and he said, “Well, Rosie, how many mayors do you know that become President?”

—RoseMarie Terenzio

By July of 1999 he had concluded he would focus on running for governor of New York in 2003. Had the stars aligned, I’m pretty convinced that’s what he would have pursued.

—Brown classmate Gary Ginsberg, now a Time Warner senior executive

John F. Kennedy Jr. Barry King/WireImage

AN ANGUISHED FINAL SUMMER

John’s cousin Anthony Radziwill had cancer for 10 years. They just kept cutting him open and taking the tumors out. By the summer of 1999 they knew they couldn’t do any more surgeries. One day John said to me, “I don’t know if I’m going to survive Anthony’s death,” and he started to cry in his office. I’d never seen him break down, ever. It was so heartbreaking.

—RoseMarie Terenzio

A MONTH LATER, JOHN WAS GONE

I gave him his first flying lessons. About two weeks before he died, I said, “You now have just enough hours to be overconfident. You need to learn to be prepared for different visual conditions. The important thing is, if you can’t see the horizon, don’t look for it.”

—longtime friend John Perry Barlow

On July 16, JFK Jr.’s plane went down. Investigators believe the crash was caused by “spatial disorientation” — and that the haze had obscured the horizon. John once told me, “Everybody expects me to be a great man, but plenty of great men were not particularly great at home. Even my father was no model. I think it would be a more interesting challenge to be a good man.” He was so good. Extraordinary, hilarious, kind. John’s friends want him to be remembered because he was the best man we ever knew.

—John Perry Barlow