Live:
LP/Strat>
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Thomas Organ Co. Crybaby wah >
Dunlop Uni-Vibe >
Maestro Phaser >
Rat (big original box) >
Tech21 XXL >
Foxx Fuzz/Wah/Volume/Octave (I only use the Fuzz) >
Digitech Delay pedal >
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Ampeg V4 / Sunn 4x12
Studio:
LP/Strat/Ibanez/cheapass Yamaha>
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Thomas Organ Co. Crybaby>
Line6 Distortion Modeler>
Foxx Fuzz/Wah/Volume/Octave>
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Line6 Pod
Live, I go way over your 5 pedal limit. But I honestly find a use for everything. (And I don't even use a pedalboard! none of the old-school pedals would fit on one anyway.) This setup gives me the tools I need to get totally clean, totally juicy, or totally heavy... Also, it's very loud. I think the V4 with the 7027 tubes weighs in around 150 watts.
I can't imagine gigging with less than 2 or 3 distortion pedals, if you play music with a lot of stylistic variation. Someday I imagine I'll use the Line6 distortion pedal for everything, but the Foxx fuzz is just the heaviest thing ever, totally unmatched. Plus, it was made in the 70's, and it's covered in red velvet.