JFK Jr. Was Crowned PEOPLE&x27;s Sexiest Man Alive in 1988: Read the Cheeky Cover Story People StaffSun, March 1, 2026 at 11:00 AM UTC 1 John F. Kennedy Jr.; 1988 PEOPLE coverCredit: Barry King/WireImage;People In 1988, PEOPLE named John F. Kennedy Jr. the Sexiest Man Alive after a picture of him playing football in Central Park shirtless came across PEOPLE's then Executive Editor Jim Seymore's desk. The crowning was befitting for the time, and according to JFK Jr.'s Brown classmate and friend, the Kennedy heir was "thoroughly amused." Now, nearly 40 years later, JFK Jr.
JFK Jr. Was Crowned PEOPLE's Sexiest Man Alive in 1988: Read the Cheeky Cover Story
People StaffSun, March 1, 2026 at 11:00 AM UTC
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John F. Kennedy Jr.; 1988 PEOPLE coverCredit: Barry King/WireImage;People
In 1988, PEOPLE named John F. Kennedy Jr. the Sexiest Man Alive after a picture of him playing football in Central Park shirtless came across PEOPLE's then Executive Editor Jim Seymore's desk. The crowning was befitting for the time, and according to JFK Jr.'s Brown classmate and friend, the Kennedy heir was "thoroughly amused."
Now, nearly 40 years later, JFK Jr.'s high-profile life has found its way back into the zeitgeist with FX's Love Story: John F. Kennedy Jr. and Carolyn Bessette, a limited series depicting the romance between the political heir and Calvin Klein associate. JFK Jr. and Carolyn Bessette met in the early 1990s and eventually tied the knot in 1996. Nearly three years into the marriage, their lives were tragically cut short by a fatal plane accident in July 1999.
Here's a look back at PEOPLE's unfiltered 1988 cover story that crowned John F. Kennedy Jr. the Sexiest Man Alive, showing a cheeky glimpse into the late JFK Jr.'s life as a 27-year-old law student in New York.
"He has something that no film star, no athlete, can duplicate — the aura, the excitement that charges a room when he enters it, simply by virtue of being Kennedy."
Okay, ladies, this one's for you — but first some ground rules. GET YOUR EYES OFF THAT MAN'S CHEST! He's a serious fellow. Third-year law student. Active with charities. Scion of the most charismatic family in American politics and heir to its most famous name.
Get your eyes off that man's extraordinarily defined thighs! What do you think, he strips down to his shorts for a game of touch football in Central Park so strangers can gape at them? They are fantastic, though. Measure three, four feet around. Legend has it that if he lived in Tahiti, instead of Manhattan, he could crack coconuts with them.
Get your eyes off that man's derriere! We saw your gaze wandering back there. It is true that columnist Liz Smith has noted that the boy "has gorgeous buns," but you've got to remember: He has a mind too. This is one hunk who won't be trifled with. Report that he is being courted as a talk show host, as a New York paper once did, and you'll get a call from the family attorney, reminding you that the son of the 35th President of the United States is not interested in showbiz, that he is a "full-time" law student and that he is "pursuing his studies very seriously."
So before we introduce John F. Kennedy Jr., 27, crown him this year's Sexiest Man and stand him a drink (he likes tequila), we want to remind you of the following: He spent the summer learning law at a very prestigious Los Angeles law firm. He attends roller-skating parties to raise funds for the inner city. He introduced his uncle Teddy (D-Mass.) at the Democratic National Convention in Atlanta and made the crowd misty-eyed and nostalgic. He is — and we want you to note we are saying this three times now — a law student, at New York University, no less, a major university. Now you can look at his tushie.
1988 PEOPLE cover
John F. Kennedy Jr., unlike PEOPLE's previous selections as Sexiest Man of the Year — Mel Gibson, Mark Harmon and Harry Hamlin — isn't a professional actor. He doesn't make his living by being on public display. The folks around him argue that he is a private citizen, and his mother, Jacqueline Onassis, has gone to some lengths to keep the press away from her family. But he has been in the public eye for more of his life than any other figure except members of the British royal family — from the time we knew him by his private family name, "John-John," and watched him — as a 3-year-old boy — stand with his mother at the funeral of his father. The nation has followed his life through his studies at Phillips Academy in Andover, Mass., and on through Brown University, from which he graduated in 1983 with a B.A. in history.
When did we first notice his spirit? When, at 14, he belted paparazzi with snowballs on the slopes at Gstaad, or when, at 16, he spent three days alone on an uninhabited island off Maine during an Outward Bound project?
When did we first notice his social conscience? No, forget it. You really don't care about his work for his aunt Jean Kennedy Smith's Very Special Arts program for people with learning disabilities, or that he's considered a friendly, decent, remarkably down-to-earth guy who once followed a stranger down the street to return the five bucks the man had dropped.
You'd rather hear some wild tales about his showing up at a Halloween party in Manhattan at 3 a.m. last year as Golden Boy, covered in glitter, or how at Brown, he and his roommate kept a baby pig in the basement of the Phi Psi fraternity house.
There were some "obnoxious types" in the fraternity, an old frat brother says, "but John wasn't one of them. At Brown he was very undercover, and he didn't have any attitude."
What was that, C.W. in Tulsa? You want to know what he looks like naked?! The entire city — no, make that the entire state of Oklahoma — will go to its room and read Profiles in Courage by John F. Kennedy Sr. and not continue this story until you have finished.
The rest of the country may continue reading to see what life is like for this year's Sexiest Man Alive.
Morning in Manhattan, and John F. Kennedy Jr. awakens in his triplex Park Avenue penthouse, gets out of his queen-size brass bed and makes his way through half a dozen nubile representatives of America's Old Money to the Jacuzzi ...
The preceding paragraph, except for the description of the bed, is totally false, by the way. We just threw it in to show you, by contrast, how exceedingly normal, in some ways, the life of John Kennedy Jr. is.
John F. Kennedy Jr.Credit: Lawrence Schwartzwald/Sygma via Getty
He lives on the Upper West Side of Manhattan, in a messy, book-filled apartment. He prefers to get around, even in winter, on his bike. He is not, in the manner of some other much-photographed young men, a male prima donna: He not only jokes with paparazzi, he's been heard to warn them when they're going to step backward into a pothole. Unlike his mother and sister, Caroline, 30, he seems to enjoy the spotlight. He's been an amateur actor since college, and when he goes for a hamburger at his favorite spot, Jackson Hole on Columbus Avenue and 85th Street, he sprawls at an outside table. Friends say he's a ham, but a lovable ham. At the L.A. law firm of Manatt, Phelps, Rothenberg & Phillips, where he just finished a stint as an $1,100-a-week summer associate, he got along with everybody. "He was one of the guys," one attorney says. "If you didn't know who he was, you wouldn't know who he was, if you see what I mean."
On the other hand, he is not one of the guys. It is not merely his looks — his mother's dark eyes and his father's striking body. (He's 6 ft. 1 in., 187 lbs.) It is that he has something that no film star, no athlete, can duplicate — the aura, the excitement that charges a room when he enters it, simply by virtue of being Kennedy.
The energy, however, hasn't inflated his ego. "I used to pay my rent to the 42nd Street Development Corporation, which was co-founded by Jackie Onassis," says Manhattan restaurateur Jean-Claude Baker. "JFK Jr. was in the office once, wearing big Texas boots with his feet up on the desk. When he saw me, he stood up and said very politely, 'Yes, can I help you?' There is no arrogance in the guy."
This is not to say that, in style and taste, he is a turncoat to his class: He is a prep. And preps do not shlep. When he couldn't get a first-class ticket to West Palm Beach last year, he bought two coach seats: one for himself and one for his guitar. He works out at the Plus One Fitness Club in SoHo, where Cher and Bernadette Peters are also $6,000-a-year members. Many of his close friends — as well as his girlfriend, actress Christina Haag — are haut monde types from Brown.
He loves to party. During the Democratic convention, he went dancing with Ally Sheedy and Rob Lowe at Rupert's, a local club. Once, on a friend's birthday, he sent a stripper to the guy's office. He does, however, have one sober habit: So he won't have his pocket picked, he attaches his wallet to his pants with a little chain.
His style of dress, when he's not suited up to escort his mother, is the aggressively bad taste best described as trust fund funk. John arrives at school in sweats and backpack and his bicycle helmet, or he shows up for an exam in a bright lime-green shirt — an extension, one might say, of the preppy ethos: Except at Racquetball, Never Let 'Em See You Sweat.
"He's interested in school, but he takes things in stride," a classmate says. "He's not one of those guys with a load of books, running around worrying that he's going to get a bad grade." How bright is he? He's certainly not much of a speller. A cheerfully scrawled invitation to his 25th-birthday party at New York's Nirvana Club 1 asked guests to come to the "lessor of two evils." His devotion to his studies, nonetheless, seems sincere; once in Torts class ...
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John F. Kennedy Jr.Credit: Ron Galella/Ron Galella Collection via Getty Images
What was that, B.W. in Daytona Beach? You say, "The heck with torts, what does he look like in Bermuda shorts?" Okay, readers, just for that, you're not going to hear one thing about his love life until you read and memorize some serious information about JFK Jr.
1) It is not easy being JFK Jr. at NYU. "People don't know how to approach him," says one woman classmate. "I've sometimes heard [prospective] employers use up the whole 20-minute interview talking about him. A few women employers have said, 'Gee, I'd love to get him into our firm.' "
2) While Democratic Party insiders do not believe JFK Jr. will seek a career in politics, no one disputes his popularity. Though privately he was nervous, his introduction of Senator Kennedy at the Democratic convention got a two-minute standing ovation. "I can't remember a word of the speech," says conservative Republican consultant Richard Viguerie, "but I do remember a good delivery. I think it was a plus for the Democrats and the boy. He is strikingly handsome."
3) During his summer job at the law firm (one of its founding partners was Ted Kennedy's law school roommate), JFK Jr. did not, like some summer associates, turn down assignments. He worked, according to one attorney, on "anything he was given."
Caroline Kennedy Schlossberg, her brother John F. Kennedy Jr., and their mother Jacqueline Kennedy Onassis.Credit: Getty
And now, on to the women.
As yet unlike his father and grandfather, who were legendary ladies' men, JFK Jr. has long relationships with his girlfriends. For four years, he dated fellow Brown student Sally Munro, 27, who resembles his sister, Caroline.
His steady for the last two years has been another Brown alumna, Christina Haag, 27, daughter of a marketing executive. A graduate of the upper-crusty Brearley School in Manhattan, Christina has known Kennedy since they were both 15. She too is Catholic; like Kennedy, she loves to keep in shape. They've acted together, playing the young lovers in Brian Friel's Winners at Manhattan's Irish Arts Center in 1985. This summer, when Haag appeared in a one-act comedy, Sleeping with the Past, at Hollywood's Tiffany Theater, she and JFK Jr. shared a house in Venice. "They bring out the best in each other," says Robin Saex, the play's director and one of Christina's closest friends.
There was no question, this summer, that Christina was Kennedy's girl. But last year, when they were dating, Kennedy was seen around Manhattan with other women as well: He showed up at a hangout on East 36th Street, Zanzibar and Grill, according to one Kennedy watcher, with a "pretty funky" Madonna look- alike. (But not the real Madonna, as alleged in the tabs. "They barely know each other," says the singer's spokeswoman.)
He was also spotted a few times with Click model Audra Avizienis, 22. "We've been on a few dates, but I'm not seeing him," says Avizienis. "I'm not a girlfriend. He has a girlfriend. Or have they broken up?"
Did she find young Kennedy sexy?
John F. Kennedy Jr.Credit: Getty
"Oh, yes," she says. "He has this quiet sadness. There's something pensive and sad about him." So how does she explain all the partying? "Well," she says, "there's that side to him too."
One cannot, of course, hold the Sexiest Man title forever. Another year, another set of Perfect Pecs. What, then, does Kennedy's family believe his future holds?
Senator Kennedy believes that his nephew will one day be involved in public affairs. "Not necessarily running for office," he said at the time of the Democratic convention, "but trying to make some sort of contribution."
Cousin Bobby Kennedy echoes that belief. "He has a tremendous sense of duty and responsibility," says RFK Jr., who now practices environmental law in Mount Kisco, N.Y. "Whenever any of the cousins need help on one of their [charity] projects, John always participates."
And as a neighbor who has watched John around the Kennedy family compound in Hyannisport observes, "He used to walk to the post office every day, just after he'd taken a shower. You could tell he wanted attention. He'd wear just a towel wrapped around his waistand no shirt."
Wait a minute! Stop that quote! This person isn't a member of thefamily, he's a gossipy neighbor!
But hold on. What's that he's saying?
"He wears the towel practically around his ankles."
Oh, good heavens!!!
"We've never been able to figure out if he's wearing a bathing suit. He's got an extremely good body."
What's that, Akron, Detroit, Cleveland, Paducah, Wichita and Des Moines? You want another look at that body? You want to see that body now?
Hey, why not? JFK Jr. has always been America's favorite son. How terrific, now, he has grown into its sexiest.
— Written by Joyce Wadler and reported by Victoria Balfour in New York with the Los Angeles and Washington, D.C., bureaus
on People
Source: "AOL Entertainment"
Source: Entertainment
Published: March 1, 2026 at 08:09AM on Source: PRIME TIME
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