Before Kobe Bryantmade his legendary mark on the basketball court, he made a pretty baller move off of it.

He was 17 and getting ready to graduate from Lower Merion High School, in the Philadelphia suburb of Ardmore. And although the top-rated high school basketball player in the country had an upcoming NBA draft to think about and had just signed a $2 million Adidas contract, first things were first: Finals, graduation, who to take to the senior prom...

As would continue to be the case down the road as he hit one career milestone after another, the former homecoming king set the bar sky-high when it came to getting a date.

Bryant had met singer and actress Brandy Norwood at the Essence Awards that April at Madison Square Garden, and was instantly smitten. "He came home from the Essence Awards and said, 'I met such a nice, beautiful, intelligent, sweet person,'" Kobe's mother, Pamela Bryant, told the Philadelphia Daily News that year.

But he was also a little shy, and Bryant reportedly asked someone else to get in touch and see if the 17-year-old Moesha star would want to go with him.

"We were in English class together, and he had one of those teen magazines and it had a picture of Brandy because she was on that show, Moesha," former classmate, friend and neighbor Ashley Pietropaolo recalled to the Philadelphia Inquirer last month. "He showed me and he said, 'I'm gonna bring this girl to prom.' And I was like, 'Whatever, you're crazy.'

"Every day, he would be like 'I'm bringing this girl to prom.'"

After Bryant was killed in a helicopter crash along with his 13-year-old daughter Gianna and seven others on Jan. 26, Brandy waited several days to collect her thoughts before weighing in on the tragedy. And even then... what was there to say?

"Never will I understand," she wrote on Instagram alongside an artist's rendering of Kobe and Gianna. "My condolences to @vanessabryant, and all families who are in pain during this tragic time. Love. #Mamba #Mambacita."

Almost 24 years ago, of course she had said yes to prom night with the NBA-bound athlete.

Brandy, who was born in Mississippi but moved to California when she was little with her parents and brother Ray J, had left Hollywood High School after ninth grade in favor of private tutoring, and therefore had no prom of her own on the horizon.

So when she got the call on behalf of Kobe, she did want to go—but had to ask her mom first.

"I thought he was cute," Brandy told the Philadelphia Daily News at the time about first meeting Bryant. "I read about him after I met him. And then I saw he was going somewhere in life and I thought I would  love to go to the prom with him."

Although it wasn't quite that simple. "I said, 'I don't know this guy,'" Brandy's mom, Sonja Norwood, relayed her reaction to the Daily News. "I had no idea who he was. And then Brandy said, 'He's a basketball player.' And I said, 'So?'" However, she added, "I liked that he had involved parents and he was doing well academically. He seemed to be a pretty good kid. He was levelheaded and grounded. And I said OK."

Pamela Bryant remembered Brandy calling and saying, "'My mom might let me go.' I thought it was so sweet." (Sonja, incidentally, also made the trip to Philly with her daughter.)

Brandy, Kobe Bryant

Bruce Cotler/Globe Photos/ZUMAPRESS.com

The famous pair naturally were all anyone could talk about before the big night at the Bellevue Hotel in Philadelphia. "It's been difficult. Very difficult," an unnamed secretary told the Philadelphia Inquirer in the week leading up to the May 25 prom, referring to the rumors (such as that Brandy was going to sing), media requests, security concerns and all the rest of the highly irregular pre-prom activity taking place.

According to the Inquirer, Kobe and Brandy arrived on the late side in a white stretch limo they shared with a group, including Kobe's teammate Jermaine Griffin and his date, Tarvia Lucas, daughter of the Philadelphia 76ers' coach at the time, John Lucas.

Some people asked Brandy for autographs and to pose for photos, but despite all the reporters gathered outside to cover the event, pictures of them from that pre-camera-phone night were relatively scarce for years (though more have surfaced in the past couple weeks). They posed gamely for the school paper photographer, Stacy Moscotti, who was told in no uncertain terms just how important getting the shot was. Otherwise, Kobe and his date were treated almost like a couple of regular kids—at least once they were inside.

"They looked just so happy," Moscotti remembered to Access Hollywood last month. "Both of them have these thousand-watt smiles, and it's just a beautiful picture."

Ashley Pietropaolo, the friend who was skeptical when Kobe said he'd get Brandy to go to prom with him, told the Inquirer that the singer was "the sweetest person I ever talked to."

Brandy remembered the night most fondly, too.

"It was so different for me to be around my peers, because I didn't go to high school," the Cinderella star told People in 1998. "We had a wonderful time."

At the same time, "it was hectic," she later told TMZ Sports, when they caught up with her during "prom season" in 2014. "'Cause, I mean, all of the press and media were there, but it was so much fun to be around kids my age, to dance and do all that."

After the dance, Kobe, Brandy and some friends went to Atlantic City for a late dinner and, Brandy later divulged to the Philadelphia Daily News, "I pecked him twice. His lips were so soft."

Despite initially saying she no longer had her prom ensemble, she indicated in 2016 that she had kept her on-point Moschino gown from that night, while the white and green corsage Bryant gave her was at her mom's house. (Either could be true: Brandy told E! News in 1998 that she thought that "keeping stuff that you've already worn is bad luck. I have a thing with that, like, I won't wear the clothes that's given to me on Moesha because, I don't know, I just think it's bad luck. I have a theory.")

Their friendship endured for awhile after the prom, the logistics made easier when Bryant was drafted by the Charlotte Hornets and immediately traded to the Los Angeles Lakers, where he'd spend the entirety of his 20-year career. Bryant's whole family moved to L.A. with him and at first they all lived together at his house in Pacific Palisades, and Brandy became friendly with Kobe's sisters, Sharia and Shaya

She and Kobe attended the premiere of the Arnold Schwarzenegger action flick Eraser together that June. Kobe then made his acting debut on an episode of Moesha in September 1996, a month before making his regular-season NBA debut at 18.

Brandy, Kobe Bryant

Mirek Towski/DMI/The LIFE Picture Collection via Getty Images

Naturally it was assumed that they were dating.

"They're just friends," dad Joe Bryant assured People in early 1997. "She comes to games, and she's friends with his sisters, but it's nothing romantic."

Chatting with Vibe in June 1996, in fact, Brandy said she was "dying to go out with Larenz Tate" and she joked that she had a slew of basketball players she wanted to marry, but Bryant didn't make the list. "I love Michael Jordan...definitely Magic Johnson and definitely Shaquille O'Neal," the teen said.

A deeper relationship with Bryant "didn't really happen, because he was so busy and I was so busy," Brandy explained to People in 1998. She had told E! News that year that she and Monica were "looking at" Kobe and Philadelphia 76ers star Allen Iverson to be in their "The Boy Is Mine" video—but as we all know now, it was Mekhi Pfifer who did the honors as the two-timer who's about to get an earful.

Bryant may have been busy at the time signing a six-year contract extension worth $70 million. 

Bryant would meet his future wife, Vanessa Laine, in November of 1999, and in 2002 Brandy welcomed her daughter, Sy'rai Iman Smith, with then-boyfriend Robert "Big Bert" Smith.

Vanessa Laine Bryant, Kobe Bryant

Alberto E. Rodriguez/Getty Images

In 2003, a 19-year-old employee at a hotel in Colorado where Bryant had been staying after undergoing knee surgery accused the Lakers star of raping her, and he was charged with sexual assault. He admitted to committing adultery but insisted that he thought the sex was consensual, though he had come to understand, he said, that his accuser did not see it that way. The criminal charges were eventually dropped when the young woman refused to testify, and a civil lawsuit she filed was settled out of court in 2005.

In 2004, Brandy told MTV News that she hadn't talked to Bryant in "so long," but she wanted "Kobe to be OK and I hope the situation works out."

Noting that she felt the same way about Michael Jackson, who was facing child molestation charges (he'd later be acquitted), she said she was purposely avoiding following either case too closely.

"Kobe is such a good person and I want to keep that. I don't want to watch too much and try to change my mind about that," she explained. "So I think that's a cop-out, but still: I just want my own personal view of those two people."

Though their lives continued to diverge, and Brandy had her own legal issues to deal with a few years later—she and Kobe would always have prom. 

And so would all of the kids who were there that night, even the ones who didn't appreciate all the hoopla at the time.

"I think some of the kids saw it as an eye roll—our big night is being overshadowed by this event of Kobe bringing Brandy here," Jennifer Weiner, who reported on that night for the Philadelphia Inquirer in 1996, recalled to the newspaper last month. "Whatever theme the prom had—and I don't remember it—the theme ultimately became Kobe and Brandy. It ended up being the two of them. But I think for others it was like Prince Charming bringing Cinderella to the dance."

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