Conan O'Brien's Leno impression made a brief appearance last night. The voice was spot-on, while the context and physicality played up Leno's sexual bravado: the impersonation came after a joke about Leno stealing the orgasmic moment in a fictional Conan O'Brien porno—literally stealing testicular satiation from late night's redheaded child, resulting in de facto castration. That this was the rare moment that drew an impression suggests Jay Leno is most "real" to Conan when the former is robbing the latter of his manhood. It's at -0:43 here:
For Conan, losing The Tonight Show represents a loss of masculinity. To reunite with his missing testicles, Conan must first unite with a new platform and audience.
Letterman's purpose is not to mimic Jay but to emasculate him, retribution for the time Leno emasculated Letterman by beating him in the O.G. battle for The Tonight Show desk. David mocks Jay to resolve the long-term cognitive dissonance associated with a squeaky-voiced interloper taking that which Letterman believed he alone deserved—a jealousy not unlike that of an elder child, when a younger sibling takes his place suckling their mother's breast. (That's totally Freud, btw, I read it in one of the Hannibal Lecter books.) By summoning Jay Mouse's voice through his lips, Letterman exerts virtual control over an imaginary Leno. But the satisfaction is fleeting; Letterman must repeat it to comfort himself, a Buddhist monk murmuring mantras or an autistic child, rocking softly back and forth.
Jimmy Kimmel was funnier than ever in his full-body impersonation of Leno on Tuesday (technically Wednesday, since Kimmel occupies the dreaded 12:05AM time slot on ABC)
Kimmel flourishes when allowed to deny the self, suggesting deep-seated insecurities. This psychological profile indicates a toxic level of self-hate—stemming either from long-term emotional abuse (Sarah Silverman, what did you do?) or a major life failure—and kinky-ass role play in the bedroom. Delighting in his corporeal transformation, Kimmel gives warning signs that he may suffer from body dysmorphia; his own body is not enough. Also, kinda homoerotic to dress up in Jay's clothes, hair, and chin, thereby "entering" a Jay-like body, no?
Summation: Conan O'Brien is an emasculated beta male, David Letterman is an arrogant grudge-holder, Jimmy Kimmel's psyche is screwed, and ragging on Jay Leno remains a cherished American pastime.