The NBA was going through an incredible transition when the 1999 Topps basketball card set hit store shelves.
Michael Jordan had retired for the second time.
Charles Barkley and Kevin Johnson would retire at the end of the 1999-00 season.
And time was quickly running out for superstars like Hakeem Olajuwon, Scottie Pippen, David Robinson, Karl Malone and John Stockton.
In short, there was a massive change of the guard underway...
Kobe Bryant, Vince Carter, Allen Iverson, Kevin Garnett, Tim Duncan, Paul Pierce and others were busy carving out the beginnings of their incredible legacies.
And some of the rookies in this set had solid careers in front of them, too.
Shawn Marion, Baron Davis, Elton Brand, Ron Artest (Metta World Peace), Steve Francis and Wally Szczerbiak were All-Stars at least once.
And then you had incredible talents like Andre Miller, Corey Maggete, Lamar Odom and Jason Terry.
As you can see, there was a lot of star power packed into the 257-card set checklist.
And in this guide, we'll take a look at the 15 most valuable.
Let's jump right in!
1999 Topps #125 Kobe Bryant
Estimated PSA 10 Gem Mint Value: $125
The first year of Kobe Bryant's six-year, $70 million extension with the Los Angeles Lakers started with six weeks of disappointment.
It ended with the Lakers' first trophy since 1988.
Bryant suffered a hand injury during the preseason that cost him the first 15 games of the 1999-2000 season.
Los Angeles went 11-4 in his absence regardless, and adding the 21-year-old shooting guard to the fray only made them that much better.
Bryant improved by leaps and bounds in every facet of his game, earning a First Team All-Defense and Second Team All-NBA spots for the first time.
He also made his second All-Star team and concluded the year as a down-ballot MVP mention.
His numbers reflected this evolution.
The fourth-year star set new career bests in nearly every metric you can think of, including points (22.5 ppg), rebounds (6.3 rpg), assists (4.9 apg), and steals (1.6 spg).
Los Angeles was still Shaq country, but Bryant was on his way to staking his claim.
1999 Topps #23 Shaquille O'Neal
Estimated PSA 10 Gem Mint Value: $60
In 1999-2000, Shaquille O'Neal was as close to a cheat code as a player can get.
Shaq was too much force in too big of a body for anybody to stop him in 1999-2000.
Whether it was his back-and-forth with Kobe Bryant or his ability to rip opposing bigs to shreds in iso situations, the 27-year-old center was virtually unstoppable.
O'Neal won his second scoring title (29.4) and led the league in field-goal percentage for the third straight season.
He also finished second in rebounding (13.6) and topped three blocks per game (3.01) for the second and last time in his career.
It was one of the most captivating and dominant seasons of the modern era, well worth a near-unanimous NBA MVP and Defensive Player of the Year runner-up.
And it only got wilder in the playoffs.
O'Neal led all playoff performers in scoring (30.7) and rebounding (15.4) while playing nearly 44 minutes per game in a league-high 23 playoff contests.
He was the end-all, be-all for Los Angeles' first NBA title in 11 years, capping things off with an unreal 38.0/16.7 average in his historic Finals MVP performance against Indiana.
1999 Topps #66 Allen Iverson
Estimated PSA 10 Gem Mint Value: $40
Shaquille O'Neal fell one vote shy of becoming the first unanimous NBA MVP.
That vote went to Philadelphia 76ers shooting guard Allen Iverson.
"I picked the guy who was the most valuable to his team," rogue voter Fred Hickman said. "Philadelphia without Iverson was a CBA team, and if the Lakers didn't have Shaq, they would have still been a pretty good team."
Shaq bashed the late CNN sports journalist for years, but it's hard to fault Hickman for his logic.
Iverson posted the highest usage rate in the league (34.4%) by a wide margin.
He made that usage worthwhile, excelling as a one-man offensive show for an otherwise slight Philly attack that finished 25th in offensive rating.
No other player did more with less.
Iverson finished second in the NBA in scoring (28.4 ppg) and took over double the shot attempts (24.8) of his next closest teammate (Toni Kukoc, 10.6).
"The Answer" was often the only answer the 76ers had, and he singlehandedly dragged Philadelphia to a 49-33 record and the East's #5 seed.
He may not have been the best player on the planet (see: O'Neal, Shaq), but he was more important to his team's success than anyone else in the Association.
1999 Topps #105 Hakeem Olajuwon
Estimated PSA 10 Gem Mint Value: $40
Despite battling age and injuries, Hakeem "The Dream" Olajuwon continued to showcase his enduring brilliance during the 1999 season.
At 37 years old, Olajuwon averaged 10.3 points, 6.2 rebounds, and 1.6 blocks per game while shooting 45.8% from the field.
Though his numbers dipped substantially from his prime, Olajuwon remained a defensive anchor and a mentor for a transitioning Rockets squad that finished 34-48.
On the personal side, Olajuwon reached a key milestone on March 9, 2000, when he recorded his 3,000th career block, becoming the first player in NBA history to do so.
He also surpassed 26,000 career points, further cementing his legacy as one of the game's all-time greats.
The season marked his sixteenth year with the Houston Rockets franchise since they drafted him number one overall in the 1984 NBA Draft.
It also marked just the second time (1991-92) during those sixteen seasons when the Rockets failed to reach the playoffs.
He'd return to Houston for one more season before finishing off his Hall of Fame career in the 2001-02 season with the Toronto Raptors.
1999 Topps #121 Tim Duncan
Estimated PSA 10 Gem Mint Value: $40
In only his third year in the NBA, Tim Duncan solidified his status as one of the league’s premier players.
His combination of skill, intelligence, and poise made him a nightmare matchup for opponents.
The 23-year-old power forward averaged 23.2 points, 12.4 rebounds, 2.2 assists, and 2.2 blocks per game while shooting 49.0% from the field.
Duncan’s all-around play earned him All-NBA First Team and NBA All-Defensive First Team honors, marking his third consecutive season achieving both accolades.
Even though Sean Elliot missed the first four months due to a kidney transplant, the defending champion Spurs raced to a 53-29 record.
Unfortunately, just as Elliot was returning, Duncan suffered a late-season injury that kept him out of the playoffs.
Without their leader, the Spurs crumbled in the Western Conference First Round against the Phoenix Suns, losing in four.
Still, Duncan’s brilliance was undeniable as he continued being a double-double machine, recording 53 on the year.
1999 Topps #146 Charles Barkley
Estimated PSA 10 Gem Mint Value: $40
Before the 1999-00 NBA season began, Charles Barkley announced that it would be the final chapter of his legendary career.
Time was certainly not on Barkley's side as the 36-year-old forward suited up for his fourth season with the Houston Rockets and sixteenth in the NBA.
In 20 games, "Sir Charles" averaged 14.5 points and 10.5 rebounds, continuing his legacy as a double-double machine.
Though his numbers were a far cry from his MVP prime, Barkley's grit and determination remained undeniable.
Barkley's season and career looked to be finished in December 1999 when he tore his left quadriceps against the Philadelphia 76ers, his former team.
Refusing to let his career end on the sidelines, he remarkably returned for one final game on April 25, scoring 2 points and grabbing 3 rebounds in limited minutes before retiring for good.
This emotional farewell showcased Barkley's trademark toughness and passion for the game.
Though he never won an NBA championship, Barkley was an integral piece of the gold-medal-winning USA Men's teams in Barcelona in 1992 and Atlanta in 1996.
1999 Topps #82 Paul Pierce
Estimated PSA 10 Gem Mint Value: $30
After a standout collegiate career as a Kansas Jayhawk, Paul Pierce wasted no time becoming one of the Boston Celtics' all-time greats during his 1998 rookie season.
Though nobody would take the Rookie of the Year award from Vince Carter, Pierce's play was enough to finish third in the vote.
And during his sophomore 1999-00 season, "The Truth" became even more believable.
The rising star took a significant leap in his second year, averaging 19.5 points, 5.4 rebounds, 3.0 assists, and 2.1 steals per game.
Pierce's scoring prowess and clutch performances earned him widespread recognition, though the Celtics struggled to a 35-47 record.
His ability to take over games was on full display throughout the season.
On February 15, 2000, he dropped 38 points against the Cleveland Cavaliers, showcasing his offensive arsenal.
His defensive intensity also stood out, as he finished 10th in the league in steals per game.
Pierce's consistency and leadership were bright spots for a young Celtics team in transition and a preview for future championship success.
1999 Topps #98 Vince Carter
Estimated PSA 10 Gem Mint Value: $30
Toronto Raptors small forward Vince Carter one-upped his 1998-99 NBA Rookie-of-the-Year season with an All-Star sophomore effort, finishing 10th in the MVP voting and with a spot on the All-NBA Third Team.
It was a banner year for Carter and the Raptors as a franchise.
The 23-year-old was among the league's most popular players and its fourth-leading scorer (25.7).
He was also the pivot point for Toronto from a fledgling fifth-year expansion franchise to a playoff team.
Every part of Carter's second season was as productive as it was impressive.
Yet, all anybody talks about in hindsight is his iconic performance in the 2000 Slam Dunk contest.
"The dunks that he was doing up in here, man, we were 'Oohing' and 'Ahhing.'," Hall-of-Fame guard Gary Payton said when asked about his favorite Slam Dunk contest. "It's a lot of them, but that one is I think the biggest one."
Carter already had a reputation as one of the fiercest in-game dunkers ever.
Yet, his inconceivable creative bag of Dunk contest jams turned him into a legend and made All-Star Saturday Night appointment viewing to this day.
1999 Topps #114 Richard Hamilton Rookie Card
Estimated PSA 10 Gem Mint Value: $30
When Rip Hamilton tried to leave UConn after his sophomore season, Jim Calhoun was ready for him.
The beloved Huskies head coach implored his star shooting guard to stay for one more year to boost his draft stock and chase a national title.
Calhoun turned out to be right on the nose.
After falling in the Elite Eight the year before, Hamilton and the Huskies surged to the program's first national title.
Previously thought to be a fringe lottery selection in 1998, Hamilton vaulted up to 7th in 1999 with the Washington Wizards.
"For me, it's the trust factor I had with Coach Calhoun," Hamilton said. "Everything Coach has ever said to me came true, especially when you live in this world of basketball, and everybody is just selling you dreams."
Hamilton didn't take a massive leap in his first year in DC, but he gained plenty of valuable experience as Mitch Richmond's backup.
The 21-year-old played 71 games (12 starts) for the 29-53 Wizards, averaging 9.0 points (42.0% shooting, 36.4% from three), 1.8 rebounds, and 1.5 assists in 19.3 minutes per game.
1999 Topps #120 Shawn Marion Rookie Card
Estimated PSA 10 Gem Mint Value: $30
Shawn Marion was the wild card of the 1999 NBA Draft.
The 6-foot-7 forward played in relative anonymity at UNLV and entered the pre-draft process projected on the line between the first and second rounds.
And then, teams started hosting him for workouts.
Marion rocketed up teams' charts with jaw-dropping showings in running, jumping, and defensive drills.
He was an athletic freak, which showed in everything he did.
So, when the Phoenix Suns grabbed him with the ninth pick, it was no surprise that a guy previously thought to be an also-ran landed in the top ten.
"Our entire scouting department was in agreement that if we were able to get a guy like Shawn Marion (in the draft), we were going to be very happy," general manager Brian Colangelo said.
Despite missing 31 games with a knee injury, Marion played a pivotal role for the 53-29 Suns.
He played most of the season as a sixth man before moving into the starting lineup late in the year.
He averaged 10.2 points and 6.5 rebounds in 51 regular-season games and followed that up with a near double-double (9.1/8.8) in nine playoff contests.
1999 Topps #250 Kevin Garnett
Estimated PSA 10 Gem Mint Value: $30
Kevin Garnett wasn't just intense.
He was as aggressive and unyielding as any player of the modern era.
"He and I agreed never to be cool on the court," NBA Hall-of-Famer Chris Webber said. "He wasn't a fake rah-rah guy. An actor, a liar, can't do that much. To cuss yourself out that much isn't possible."
Garnett went full speed from the opening tip to the final whistle, giving maximum effort as an elite scorer and an all-world defender.
The results came and kept coming, especially during the 1999-2000 season.
Making the leap from fringe MVP candidate to the very top of the basketball world, Garnett entered his athletic prime with a massive two-way statement.
He averaged 40.0 minutes for the 50-win Timberwolves, dropping new career highs in points (22.9), rebounds (11.8), and assists (5.0) per game.
He scored at a hyper-efficient clip (49.7% shooting, a career-best 37.0% from three) from all three levels.
He defended those three levels with the same success, earning First-Team All-Defensive honors to go with his All-NBA First-Team spot.
Shaq may have been the far-and-away choice for NBA MVP, yet Garnett was as solid of a runner-up as you're ever going to find.
1999 Topps #116 Baron Davis Rookie Card
Estimated PSA 10 Gem Mint Value: $25
Now, NBA lottery picks plug in as starters immediately unless extenuating circumstances dictate otherwise.
In 1999-2000, that wasn't so much of a thing.
Drafted third overall by the Charlotte Hornets in the '99 Draft, Baron Davis was relegated to backup point guard behind seven-year veteran David Wesley.
Whether in high school or at UCLA, Davis had always been the guy.
Now, he had to suck it up and take the few minutes he was given.
"Back then it was a thing where no matter where you were as a rookie, coaches didn't play rookies," Davis said. "For me, it was the opportunity to start being a man, but also it was humbling because I was playing 19 minutes a game, no more than that."
Davis played all 86 games for the Hornets (82 regular season, 4 playoff) but did not register a start.
He played 18.6 minutes a game during the regular campaign (averaging 5.9 points, 3.8 assists, and 2.0 rebounds), before seeing his workload drop to 14.6 minutes per contest in Charlotte's 3-games-to-1 First Round loss to Philadelphia.
1999 Topps #115 Elton Brand Rookie Card
Estimated PSA 10 Gem Mint Value: $20
Some #1 picks may appear to coast on their talents, usually because they're so good that it looks easy.
It never looked easy for Elton Brand, despite how great he was.
Selected first by the Chicago Bulls in the 1999 NBA Draft, the 6-foot-9 big man found himself in a position that would become familiar over his 17-year career: the high-efficiency, board-snatching centerpiece of an otherwise awful team.
Brand had plenty of natural athleticism and brute strength to spare, but the highlight of his game was how damn hard he worked.
The New York native had a tireless motor, whether on the offensive glass or bodying an opponent in the post.
The numbers bore this out during his rookie year.
Brand averaged a double-double of 20.1 points (on 48.2% shooting) and 10.0 rebounds (4.3 offensive) to grab co-Rookie-of-the-Year honors alongside Houston Rockets guard Steve Francis.
"I have a part of it, a part of history," Brand said. "You can't be disappointed about winning Rookie of the Year. Even if it's co-winners."
1999 Topps #118 Steve Francis Rookie Card
Estimated PSA 10 Gem Mint Value: $20
When Maryland point guard Steve Francis arrived in Houston as the second overall pick of the 1999 Draft, he immediately found himself in the crosshairs of veteran teammate Charles Barkley.
Barkley got on the kid immediately, pushing him to come to the gym early and stay late.
The future Hall-of-Famer hounded Francis at every practice and wouldn't let up.
"He didn't want to see me go down the road that he did when he first came in the league," Francis recalled. "He told me about how Moses Malone and Dr. J were on his back every single day, and he didn't listen."
Francis was initially annoyed by Barkley's constant attention.
Eventually, he saw the merit.
Once it all clicked, the 22-year-old quickly blossomed into the game's best rookie guard.
A co-choice for NBA Rookie-of-the-Year with Chicago Bulls big man Elton Brand, Francis averaged 18.0 points, 6.6 assists, 5.3 rebounds, and 1.5 steals in 77 games for the 34-win Rockets.
He was one of the few things worth celebrating in a season in which Hakeem Olajuwon was limited to 44 games with a foot injury, and the Rockets missed the playoffs for the first time since 1992.
1999 Topps #231 Lamar Odom Rookie Card
Estimated PSA 10 Gem Mint Value: $20
In a season where the Los Angeles Clippers finished 15-67, there weren't many bright spots for the struggling franchise.
But Lamar Odom was one of them.
Selected fourth overall out of the University of Rhode Island, the 20-year-old forward quickly made an impact, averaging 16.6 points, 7.8 rebounds, 4.2 assists, and 1.2 blocks per game.
Odom's unique skill set as a 6'10" playmaker earned him All-Rookie First Team honors and established him as one of the league's most promising young talents.
For a player his size, he had an above-average ability to handle the ball, facilitate the offense, and impact the game in multiple ways.
The 1999-00 season was just the beginning of Odom's impactful NBA career, during which he was great but never quite an All-Star level talent.
Over his fourteen NBA seasons, he nearly averaged a double-double (13.3 points and 8.4 rebounds per game) while earning the Sixth Man of the Year award (2010-11) and grabbing a couple of rings with the Los Angeles Lakers.
1999 Topps Basketball Cards In Review
Had some of those big-name rookies made it to the Hall of Fame, this set might get a lot more love than it does.
And it didn't help that Michael Jordan retired, either.
Still, there's no question that there are many great players packed into the relatively small 257-card checklist.
And if nothing else, you gotta love those orange borders as they give these cards a unique look and feel.
As far as subsets go, there were a couple:
- Rookies (#111 - 120; 231 - 248)
- USA Men's Team (#249 - 257)
Overall, this set is fairly solid and there's no question that it was loaded with big-name players.
However, the fact that none of those rookies ever made it to the Hall of Fame will always be its biggest drawback.