Lord of the Championship Rings: Scottie Pippen vs. Pippin Took

They're two of the best sidekicks ever, and they both happen to have the same name. So, how can I not make this comparison? In the league where amazing happens, it's pretty much universally accepted that Michael Jordan was the most amazing. It's also universally accepted that Jordan wouldn't have been as amazing without his right-hand man, Scottie Pippen. Pippen was the Robin to Jordan's Batman, the Watson to his Sherlock, or the Jazz to his Fresh Prince. On the other hand, there's Peregrin "Pippin" Took, the cheerful and sometimes careless Hobbit, who served as a loyal companion to Frodo's mission and a valuable member of the Fellowship of the Ring.

To properly compare sidekicks, you have to compare the leader whom they devote their services to. In this case, it's Jordan against Frodo. Like I said, MJ is pretty much as good as it gets in terms of basketball. While you can make arguments for people like Russell and Wilt, no one's going to think you foolish for proclaiming Jordan to be the greatest. In terms of Middle-earth, though, you can hardly make the same claims about Frodo. While Jordan made big shot after big shot, Frodo tended to fall down or faint every time something stressful happened. Although to be fair, Frodo's situations were usually much more intimidating (and life-threatening) than MJ's. But in the end, Frodo did accomplish the most difficult task of all: while Jordan was racking up rings, Frodo destroyed the One that he had. While Jordan was more dominant in his field, Frodo's quest had much grander signficance as the destruction of the ring meant the end of corruption and an "evil that does not sleep."
Call him Alicia Keys because he keeps on fallin'

But this is not about Jordan and Frodo, it's about Pippen vs. Pippin. And Scottie P was Jordan's go-to guy for all six championships. Outside of these two, the Bulls didn't really have the kind of players that made you think six championships in eight years. I mean, have you ever played with the Bulls on NBA Hangtime (which features no Jordan)? Steve Kerr, Toni Kukoc, and Luc Longley are starters on the game! With that many white people, they look more like a scene out of Middle-earth than a championship basketball team. It goes to show the value of Pippen, and validates his seven All-Star appearances and Hall of Fame induction. But Pippin Took was no slouch, either. Sure, he liked to get drunk and got the Fellowship into trouble half the time, he proved to be quite a worthy companion.
Hello, my name is Peregrin Took, and I'm an alco-hobbit.

We may never know if Jordan could have won six rings without Scottie, but we know that Scottie couldn't win any without Jordan. For MJ's two year hiatus (when he played baseball/journeyed to Looney Toon Land), the Pippen led Bulls failed to reach the Finals both years, not to mention a run-in with Phil Jackson that got him seated on the bench for the final play in the Eastern Conference semifinals. Pippin Took, however, did some of his best work in Frodo's absence. He escaped from an army of Orcs, talked to a few trees (how many people can say that without being psycho?), and he even killed some Orcs and a troll by the end of the trilogy.
Jordan journeys to Looney Toon Land during his two year retirement

Both Pippin and Pippen play the sidekick role perfectly well, so the difference to me is how they performed on their own. Scottie failed to win it all in Chicago and kind of fizzled out with the Trail Blazers, while Pippin Took blazed his own trail and did his best work on his own. In the end, destroying Frodo's one ring was bigger than winning six championship rings, so this victory goes to Peregrin Took, the best Pippin of all.

PS: Now, correct me if I'm wrong because this may be purely speculation, but from what I hear, they're taking the hobbits to Isengard.