POSTED: Feb 10, 2016 7:55 PM ET
The years in between have passed in a blur.
On his final visit to Cleveland to play against James on Wednesday night, Bryant reflected on his relationship with a player who once hung a poster of him on his bedroom wall in Akron, Ohio, and has grown into a valued friend.
And as he gets ready to say goodbye to the NBA after two decades, Bryant was stunned to learn that James, too, is on the back half of his career.
"Is this his 10th year?" Bryant asked, before being told that James has been in the league longer. "Eleventh year? Thirteenth year! He's a true, true vet. It's strange. To me, it still seems like he just got into the league. Pretty crazy. ... He might retire soon, too."
Bryant was at ease during his interview session with reporters before the Los Angeles Lakers played the Cavaliers. This is Bryant's sendoff, his farewell tour, and the 37-year-old is trying to savor every moment.
When he was in high school and on the verge of becoming a household name, James met Bryant before playing against Carmelo Anthony in an All-Star game in Philadelphia. It was then that Bryant dropped some knowledge on James.
"I remember sitting down and talking with him," Bryant said. "The advice I gave him, because he would have so much coming at him, was focus on the game. Stay true to the craft. Everything else would sort out. That was the most important piece of advice I could give him."
On several occasions this season, James has spoken with reverence toward Bryant, one of the game's most celebrated players with whom he is often compared. The two didn't always have the strongest connection, but is has matured over the years, helped by them playing together on the U.S. Olympic team.
Bryant and James once seemed on a collision course to meet in the NBA Finals, but the matchup never materialized, disappointing a basketball world wanting to see the greats go head-to-head with everything on the line.
"We never crossed paths unfortunately," Bryant said. "I just wanted to win the damn thing. I didn't care who we played. For the fans it probably stinks because it would have been a great matchup, but from a player's perspective it doesn't matter who you play. ... Just want to win the championship."
Bryant recalled previous visits to Cleveland, including the 1997 All-Star Game when he participated in the dunk contest as a rookie. That year the showcased the game's Top 50 players, a who's who of hoops immortality that had Bryant in a daze.
"Man, I remember walking around the hotel, I remember walking around this arena, and just running into a great after great after great after great after great," Bryant said. "I grew up watching all of these players. So I watched all of the classic videos, the films, the books. So to see these players all walking around, it was pretty amazing."
This weekend, Bryant will take his All-Star bow. It will be the last time he mingles with his peers, who will undoubtedly honor him throughout the festivities in Toronto.
Bryant's career has come full circle.
"I can't wait to be around them and talk to them and see how far the game has progressed, see all this young talent the different generations of players," said the 16-time All-Star. "To me, LeBron is still young. I can't fathom this is his 13th season and the generations that come after him - the Durant generations, the Curry generations. There are so many generations in between that. It's going to be fun for me to be around.
"When I first played in an All-Star game, imagine an 18-year-old, 19-year-old kid walking into a locker room and here's John Stockton with his little itty-bitty shorts. There's Barkley. There's Clyde Drexler. There's Gary Payton. I was a 19-year-kid."