24. Die Another Day (2002)
You know you’re in trouble when a cameo by Madonna (as a rapier-wielding fencing instructor, no less) is nowhere near the low-point of your film. As the 20th entry in the James Bond franchise, Die Another Day was conceived as a celebration of the series’ rich history, and there’s at least one continuity nod to each previous Bond film dotted throughout the production. A nice, nostalgic idea; but instead of adding to the James Bond legacy, the resulting film is as much a parody of James Bond as Austin Powers (released five years earlier)—albeit without the laughs. Well, not intentional laughs, that is. Between Bond’s invisible car, Halle Berry’s cringe-worthy performance as Bond-girl Jinx, and an action sequence in which 007 surfs a tidal wave (yes, you read that correctly), it’s impossible to take any of it even remotely seriously. In fact, the film proved such an embarrassment to creator Ian Fleming’s legacy that it marked the end of Pierce Brosnan’s stint in the title role and put the franchise on ice for four years until it could be successfully re-booted.
The good news? It’s all uphill from here on our list!