Era: 2002-2008
As seen on: Elegantly disheveled frat bros; basic dudes with normal jobs; farmers

It takes a while to develop the expansive arsenal of untamed fuckery that Tom Brady demonstrates on a regular basis these days. Basically, you have to lock down an iconic sex symbol, lead a few dozen fourth quarter comebacks, and vaunt an airplane hangar's worth of $100 bills in your full-floor Manhattan apartment. These are Brady's swaggerless developmental years, which were apparently spent getting the walk-in side eye at Sports Clips.