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3. 101

Natas Kaupas, he of fire hydrant-spinning fame, left longtime sponsor Santa Monica Airlines to start 101 with Steve Rocco, who by that point was way ahead of his corporate contemporaries. Its riders ran the gamut from Kris Markovich to Gabriel Rodriguez to Gino Iannucci to a baggy-panted Jason Dill, and over time its ads grew more esoteric and evocative. In 1996, shortly after its part in Trilogy became everyone’s favorite section of the summer, Natas moved on and began a career as a designer.


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