#10 - Joan Cusack and Sarah McLachlan as Jessie - Toy Story 2 (1999)
Best Song: When Somebody Loved Me
Okay, this is the last truly oddball pick, I promise. Though it's not the last one that I can hear people screaming at me about in my head when I look at their relative placement on the list. Oh well.
Yes, technically Pixar's catalog counts as having been released by Walt Disney Pictures, so there is a strong argument (certainly much stronger than for Anastasia) to think of Jessie as a Disney heroine. And, for what it's worth, I think she's an excellent one. Joan Cusack goes all-out with her voice work, and though Jessie's signature "YEEEEEEEEEEEEEEEE-HAWWWWW!" might be annoying to some, I find myself completely taken in by her sheer, unabashed jubliance. Jessie, as a character, adds something to the Toy Story franchise that it was missing, as the first film had a certain (intentional) dark joylessness about it.
Now, I love the two movies almost equally, but it must be admitted that the sequel delights much more in its childish joy than its predecessor. And that's what sets 2 apart from the first and third entries in one of the greatest movie trilogies ever. 1 has the darkness and ingenuity, 3 has a plot that makes even the strongest of hearts melt, and 2 has pure, unbridled joy, in large part courtesy of Jessie.
That is, until we get to "When Somebody Loved Me". This was the first chance for the character to show some range, and unlike our other big one-song wonder so far (Esmeralda), this sudden change is rather more warranted and earned by Cusack, so it's not quite as jarring. This also marks the first huge tearjerker moment in the Pixar history, and arguably one of the most understatedly successful. Sure, everybody cites the first fifteen minutes of Up, or the incinerator scene and ensuing last 15 minutes of Toy Story 3, or even things like the end of Monsters, Inc., but through all that, everybody still remembers this heartwrenching song. The filmmakers make much less of a production of this scene than of the others, and arguably that makes it even more effective. It's an off-puttingly depressing scene, made possible by a pitch-perfect performance from the quasi-country-ish vocal stylings of Sarah McLachlan. (These sentences of mine are starting to get a bit out of hand. I swear they're breeding.)
It's a very similar situation to Esmeralda, with one key difference. What people remember about "God Help the Outcasts" (and rightly so) is that it's one of the greatest songs ever in a Disney movie. Credit to Alan Menken for that one. But they don't remember it tying in with the character. What people remember about "When She Loved Me" is Jessie's absolutely heart-wrenching story that goes along with it, and the trauma we felt as kids watching this scene for the first time. Damn you, Pixar, you've broken children all over the country with this song, and now we'll never be secure enough to give away our toys. (Though perhaps this has been reversed a bit with the even-more-heartwrenching-yet-somehow-happy-nobody-really-knows-how-to-feel-about-it ending to the series in 3.)
Anyway, before I ramble on TOO much, here's the (possibly too explicit) next HINT. Many people consider the next Disney princess to be the greatest of them all. It is also not unheard of to consider her the worst.