WWE Network’s 5 part Limited Series gives a deep insight into Mark Calaway, the man behind WWE’s legendary Undertaker character and his quest to find a proper ending for his storied career and character.

Pro Wrestling, despite its scripted nature, is not dissimilar to many sports institutions. It has its all-time greats; those who’ve become as big as the sport in the minds of its fans. Without a doubt, WWE’s version of Baltimore Orioles great Cal Ripkin Jr. is Mark Calaway, the man known to fans as The Undertaker. Both are known for their unwavering loyalty to their home team and their tenure of over 2 decades with that team. Ripken played for the Orioles for 21 years and Undertaker had over 21 years of undefeated outings at wrestling’s World Series, Wrestlemania. Both are recognized as essentially being the heart and soul of that league. But while Ripken found his ideal retirement, Calaway has not and The Last Ride chronicles his 3 year-long saga to find a perfect exit for his career that matches up to the aura and longevity of his mythical character. But with his body breaking down, did he overstay his welcome in the world of wrestling? That’s what The Last Ride explores in this 5 episode series.

Behind the scenes documentaries into the world of pro-wrestling have become a hot commodity in the last few years, with VICE’s Dark Side of The Ring being the gold standard in following up on the impact of nostalgic events and legendary characters of pro-wrestling’s yesteryear. Given the fact that WWE owns the whole of pro-wrestling history in its respective video libraries, its been long past time they take advantage in doing a series like this with one of their most popular characters. That being said, Calaway’s quest to find a perfect moment to go out on throughout the series strongly resembles an episode of Dark Side of The Ring, with Calaway seemingly addicted to the dopamine rush of performing and other wrestlers like Shawn Michaels and Paul “HHH” Levesque calling it akin to “chasing the dragon,” as whenever a good top-tier performance that would be ideal for Calaway to retire on presents itself, he takes it as proof of his having many more matches in his gas tank until the next bad match makes him wants to retire. Calaway states that he wishes he had the clarity of intent to know when to hang it up, but we follow him through 4 Wrestlemania events from 2017 through to 2020 to try and find a moment that seems worthy of his character’s legacy and not disappoint his longtime fans and their kids.

THE LAST RIDE largely works because of the strength of its first 2 episodes and the finale. The first 2 episodes chronicle Calaway’s attempts to end his career at Wrestlemania in 2017, only to have a lackluster match due to his degenerative hips and lack of ring shape that makes him question if he should have retired a few years earlier against Shawn Michaels. The following episode Redemption chronicles his attempt to get into ring shape for a match against John Cena at Wrestlemania, which he is happy with but begins a yo-yo of good matches to bad matches ratio that leads to his final match against AJ Styles at Wrestlemania amidst the Covid-19 pandemic. Even then, it seems that while Calaway is satisfied to call it a career, the lack of a crowd or ovation have made it a safe retirement for now and it stands to measure whether he’ll continue to chase that dragon for an ideal moment.

Ultimately, THE LAST RIDE is a pretty fascinating look at the struggle in ending a career on a memorable moment for an enduring character when the performer behind it is only mortal. Its not as in-depth as ESPN’s The Last Dance, but chronicles a lot of his career to give the end more relevance. There’s a bit of a curse in trying to find a great ending for a character when the man behind is struggling to live up to its legacy and The Last Ride really succeeds in showing that struggle.