The Gang: The Goonies
The Film: The Goonies (1985)
Led By: Michael "Mikey" Walsh (Sean Astin)
Enemies: The Fratellis.
Why Are They Cool? Who as a kid wouldn't have wanted to be part of a group of hilarious misfits?
They've got it all - chatterbox leaders (Astin and Corey Feldman), nerdy inventor (Jonathan Ke Quan), and lovable tubby type Chunk (Jeff Cohen), who provides most of the laughs and plenty of the heart.
With Goonies as a wish-fulfilment adventure lark, the boys might come up against a crime family, but at least you know everyone's getting out alive.
Which is more than you can say for most of the other gangs on the list...
Next: Reservoir Dogs