In a press conference to announce the details of Jay Leno’s departure from “The Tonight Show”, the comedian turned up in disguise to ask questions about his own future. Leno put on a bald cap, fake goatee and glasses and joined the real reporters quizzing NBC executives about the turnover from him, after having hosted the show for the past 16 years, to Conan O’Brien.

It was revealed that the date set for Leno’s last “Tonight” appearance would be Friday, May 29, 2009, while Conan takes over the following Monday, June 1.

To his credit, Jay has put on record early on that the transition will be smooth and hassle-free. His beating out David Letterman as host of NBC’s “Tonight” show in 1992 was fraught with drama and ill feelings, and he has been quoted as saying that “Quite frankly, I don’t want to see anybody go through that again”. Even though, as reported by Slate, the lame duck has quacked that he doesn’t want to give up his gig.

Conan has been uncharacteristically mum about the whole thing. The 1985 magna cum laude (seriously) Harvard grad (History and Literature) prefers to let things play out and allow Leno center stage in the lead up to his long good-bye. He’s also been dealing with a problem which seems to have stepped out of one of his comedy routines, involving a Catholic-priest stalker.

I like both Jay and Conan, and for some reason I can’t explain, I just don’t find David Letterman funny or even entertaining. He comes across as a mean old coot trying hard to be nice. But between the folksy Jay and the self-deprecating Conan, I guess I prefer the latter. His sketches are funnier and he has a flair for physical comedy which Leno just can’t match.

Rumor has it that Jay will eventually join either ABC or Fox, which may result in another late night war reminiscent of the Leno-Letterman tussle, but this time involving three combatants. It’ll be interesting how this one would turn out, although I predict that in a three-way battle, Letterman will be given the boot.

Meanwhile, Jimmy Fallon is all set to take over Conan’s slot and will prepare by posting short comedy sketches nightly on the internet.

Conan O’Brien’s commencement speech to the Harvard class of 2000.