Even Stevens: Heck of a Hanukkah (2000)
It was difficult to focus on this one since the lead is portrayed by an extremely young Shia LaBeouf portraying the exact same character he played in Transformers. It was actually kind of surreal.
The episode itself had highs and lows. Surprisingly, the highs were really quite good. The plot started with Louis (LaBouf) locating the Hanukkah presents and opening them early. In a botched attempt to conceal them afterward, he inadvertently destroyed them and was (of course) punished. He then wished he'd never been born, transitioning to a "Wonderful Life" story. What should have been derivative was saved by some innovative twists. When they introduced the "guardian angel" stand-in as a stereotypical old Jewish grandmother, I cringed for the worst, but I was pleasantly surprised. Good writing made the character work, and she wound up delivering most of the laughs.
Likewise, the alternate reality initially seemed superior: there was another son in Louis's place, and at a glance, he was a better kid. As he stayed longer, he discovered his replacement was a horrible, sadistic person. This led to some good sequences.
Unfortunately, there were also lows: the episode had a tendency to devolve into incoherent sequences, most of which were stranger than they were funny. The worst of these had Shia LaBouf running around with a raw chicken on his head. In addition, the resolution to the alternate universe was unsatisfying.
This is the best Hanukkah special, episode, or movie we've done for the blog to date, but that's probably the lowest bar in existence (I just said this was better than Lamb Chop or Eight Crazy Nights: so are most surgeries). It was certainly interesting, and a case could be made for good. At the very least, it was a hell of lot better than I'd expected.