CC Sabathia is next, as the standout left-hander is scheduled to make an appearance on "The Jay Leno Show" on NBC when he joins Leno via satellite for the segment "Ten@Ten" on Friday.
Jeter, Pettitte and Posada strolled into Letterman's CBS show sharply dressed in suits and ties -- Jeter in black, Pettitte in gray and Posada in Yankee blue -- and faced a variety of topics.
Letterman described the span from 2004-06 when Pettitte interrupted his Yankees career to play with the Astros by saying he "left for three years to go run a 'Dairy Queen' or something."
Then he asked how close the 37-year-old free agent is to retiring.
"I'm getting close," Pettitte, the Game 6 winner, said. "If I pitch one more, that would probably be good. I'm not real sure yet what I want to do, but I'm definitely close to the end. I've got kids that are getting older -- one in high school now -- and I really would like to be home with them a little bit."
He asked Jeter if he could play shortstop in his 50s and whether or not he is engaged -- the Yankees' captain dispelled the engagement part quickly -- wondered out loud to Posada, "How long can a grown man squat?" and questioned why nobody has been able to figure out Mariano Rivera and his devastating cutter yet.
"It's unbelievable what he's been able to do," Jeter said. "No one's ever been able to do it before, and in my opinion, I don't think they'll do it again."
Posada, Pettitte, Jeter and Rivera all pretty much came up together in the Yankees' system and have won five World Series rings together. One man who saw them blossom into the standout Major Leaguers they are today is Joe Torre, who managed the Yankees for the last time in '07 before taking over as manager of the Dodgers.
Letterman half-jokingly asked if the Yankee players were a little shaky about current manager and ex-teammate Joe Girardi taking over after the club missed out on the playoffs in his first year last season.
"We had a lot of injuries last year," Posada explained. "It was a learning experience, obviously, for Joe, but he showed a lot this year. He really was great during the postseason -- setting up the pitching staff, the bullpen was fresh as it can be to the postseason -- and that's the reason we're here."
At the end, Letterman brought out World Series Most Valuable Player Hideki Matsui, who greeted the famous host with the World Series trophy.
On the NBC side, Chamberlain stopped by Fallon's set. But he got a little more involved than his teammates.
The hoarse Yankees right-hander popped in to play a little bit with "The Roots," Fallon's band on the show. The Grammy Award-winning group is from Philadelphia and agreed that if the Yankees won the World Series, they'd let one of their players play a melody with them.
So Chamberlain came through the blue curtains, took the stairs to the second level where keyboardist Kamal Gray was stationed -- "Did you thank Jimmy Rollins, by the way?" Chamberlain said to him -- and learned to play an easy tune that turned out to be part of the song "Empire State of Mind," which Jay-Z and Alicia Keys performed at Yankee Stadium before Game 2.
"I can't really talk," Chamberlain said upon making his entrance to the show. "It was fun. To put into words what we did, it was special."
Of course, no late-night talk show is complete without a comedic monologue. Here were a few Yankees-related zingers courtesy of Letterman:
"Long season, brutal season, 162 games, 40 or 50 playoff games, and then the best of 30 in the World Series. Finally, now, they get a well-deserved rest, and then on Monday they report to Spring Training."
"The Yankees, your world champion Yankees, they have to make a big decision in the offseason -- are they going to keep Kate Hudson or sign Drew Barrymore?"
"I'm going to be hosting for eight commercials, and then we bring in Mariano Rivera."