If Bryant manages to climb that mountain for a sixth time, he moves ahead of Magic Johnson as the unquestioned best Los Angeles Laker in franchise history, as Magic only earned five titles in his time as a Laker.
With that sixth championship, Bryant would match the ring total of none other than His Airness, Michael Jordan.
How's that for high stakes heading into a season?
Bryant knows what a sixth ring could mean for his legacy. While there may never be another Jordan, a player like Bryant matching (or even exceeding) M.J.'s championship count puts him at least more soundly in the greatest-of-all-time discussion.
Let's look at the tale of the tape between the two superstars for a moment.
Jordan finished his 15-year NBA career with six championships, six NBA Finals MVP awards, five regular season MVP awards, one Defensive Player of the Year nod and the 1984-85 Rookie of the Year award.
He led the league in points per game a ridiculous 10 of those 15 seasons, including a run of seven straight years from 1986-87 through 1992-93, right before his first retirement.
In the playoffs, he only got better. In all but three of his 13 playoff appearances, Jordan led the NBA in points per game, starting off with an unbelievable 43.7 PPG average over three games in the 1985-86 playoffs.
The top 10 list of Jordan's Finals plays, according to NBA.com.
Bryant, the Black Mamba, can't quite compare to that long list of accolades. His five championship rings come close to measuring up to Jordan, but he's only got two NBA Finals MVPs and one regular season MVP to his name, compared to Jordan's six and five, respectively.
The scoring titles comparison is even more lopsided, with Jordan's 10 to Bryant's two. Bryant did lead the league three times in playoff points per game, but again, can't begin to measure up to Jordan in that regard.
Long story short: Even if Bryant wins a sixth (and seventh?) ring in the next few years, he'll never be able to match Jordan's bevy of NBA awards and scoring titles.
A sixth ring would give Bryant one advantage over M.J., though. Unlike Jordan, who won his six championships all within an eight-year time frame, Bryant would have three rings a piece from two distinctly separate eras.
Jordan was always the alpha dog for the Bulls when he won all six titles, had Scottie Pippen as a sidekick for all six, and had Phil Jackson as a head coach for all six.
Bryant, on the other hand, has Shaquille O'Neal and Jackson to thank for his first three rings, while he'd be splitting credit between Pau Gasol, Andrew Bynum, Jackson and new Lakers coach Mike Brown for his latest three.
Already, Bryant's career longevity is giving him more and more of an advantage over Jordan, who only played 15 seasons in the NBA. Bryant is going on his 17th and finished second in the league in scoring last season.
Even after 16 seasons, the Mamba remains one of the league's most feared scorers.
If Bryant can stay healthy and keep his groove on for the next few seasons, he's going to pass Jordan on the all-time points list. Jordan scored 32,292 points over his 15-year career; Kobe's on 29,484 and counting.
In all likelihood, Bryant will pass that mark sometime during the 2013-14 season. He's 2,808 points shy at the moment, and hasn't scored fewer than 1,500 points in a season since 1999-00.
Passing Jordan in all-time points will only further the Bryant vs. Jordan debates, but there's one noted area where Bryant falls short in comparison: shooting efficiency.
Jordan shot an incredible 49.7 percent from the field over his career, averaging 50 percent for a five-year streak that ended with his second NBA championship. That's unbelievable efficiency for a player taking 20-25 shots per game.
Bryant's overall career shooting average of 45.3 percent isn't bad by any stretch of the imagination, but it's not Jordan-esque. Bryant's career-high from the field came back in the 2001-02 season, when he shot 46.9 percent overall.
Jordan only finished below that mark five times in 15 years. Three of those seasons occurred after he came out of either his first retirement (1994-95) or his second retirement (2001-03).
Both Jordan and Bryant will be remembered as volume scoring shooting guards, hence all of the constant Kobe vs. Michael comparisons, but Bryant's efficiency doesn't come close to matching Jordan's.
That, more than anything, will always give M.J. the win over Bryant, no matter how many rings Kobe amasses in the next few seasons.