Now, 20 years later, he's gracing the cover again - only this time, he's sharing the spotlight with his two sons, 17-year-old Bronny and 15-year-old Bryce.
In a new interview with Sports Illustrated, the 37-year-old Los Angeles Lakers star talks about his life as a dad and the possibility of Bronny joining him on the NBA court. He's occasionally said he intends to play on the same team with Bronny when his son reaches the league.
Although plenty of obstacles remain between the younger James and the NBA, he could be draft-eligible in the summer of 2024.
While Bronny is hopeful, he's preparing for anything, saying he'll "see what happens."
"I'm going to be playing basketball. If [I] go down that path, then it is what it is."
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He said if the NBA doesn't pan out, he's "cool."
Bryce, on the other hand, is four years from being draft-eligible. By then, James will be 43. Even at that age, he could well be on the court with both of his sons.
The star told Sports Illustrated, "It's all up to my body, but more importantly, my mind. If my mind can stay sharp and fresh and motivated, then the sky's not even a limit for me. I can go beyond that. But we shall see."
Some have said James is placing unfair expectations on his sons, but the athlete said he's unfazed by the criticism, saying "our quest and our journey is not predicated on what everybody said."
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So will the boys go straight to the NBA or play ball in college? James said for now, he wants his sons to go the college route, but two years is a long time.
Only time will tell.
The latest issue of Sports Illustrated will be available on Sept. 15.