10. Escape To Victory
Going to get this one out of the way early because otherwise I'll have your dad in the comments demanding to know where it is. "Better than The Great Escape Son! Bobby Moore's In It! Proper player him! And that Pele fella advertises that medication your old man here likes!". If you're wondering where Shaolin Soccer, Air Bud, or Bend It Like Beckham are in this list, consider their spiritual spot this one.
Anyway the premise here is that "The Allies" are captured by the Nazis and, for reasons that are never made abundantly clear, have to play them in a glamour friendly in Paris. Michael Caine (yep) guides his ragtag team of Pele (yep), Bobby Moore (yep), Ossie Ardiles (yep), Sylvester Stallone (yep) and half the Ipswich Town first team (yep?) against the highly drilled forces of the Reich.
Not to spoil the ending, but legend has it that Stallone had it written into his contract that he had to score the winning goal. Sure, fine, makes sense, until you realise that he's actually cast as the goalkeeper. A hasty rewrite ensued, the climactic scene became a penalty shootout, and Sly got to quite literally save the day. U-S-A!