I don't remember the exact date or show (either Letterman or Leno), but I do distinctly remember watching Third Eye Blind perform "How's It Going to Be?" while promoting their highly successful eponymous debut album. This means that the performance took place around 1997-98, which would make me about 15-16 years old at the time.
Holy jeebus I can't believe how easy it was to find the exact performance I was thinking of in internet video format.
My point is this: even at the time I was most ardently a fan of 3eb ('97-98), this performance with the bare feet & leather straitjacket struck my teenage self as incredibly ham-fisted. With age comes wisdom, however, and now in 2010 I've finally acquired the single adjective that most succinctly defines this performance:
Douchey. This is a super-douchey move.
Seriously, at about the 2:20 mark it gets pretty awkward.