"This is something Jay asked me to do," Taylor said in a telephone interview from his town of Washington home and studio. "It's a great honor."
Leno is only the fourth host since "Tonight" made its debut in 1954 with Steve Allen, followed three years later by Jack Paar and then, for 30 seasons, Johnny Carson. Leno took over in 1992; next September, his new one-hour "Jay Leno" show will be televised weeknights at 10 in what's considered a landmark programming shift to combat declining audiences for network TV. O'Brien takes over "Tonight" this Monday.
Leno, who was raised in Andover and graduated from Boston's Emerson College, explained his choice of Taylor in a recent conference call from Hollywood.
"When I left Boston in the early '70s," Leno recalled, "James Taylor was playing on the radio and I said, 'Well, I'm gonna go to Hollywood and see what happens.' And last year, I asked James Taylor, we had this discussion, I said, 'Hey, for the last show? It'd be great. ... You know, you were the last thing I heard when I left town and it would be great. ...' Because he's a Boston guy and he said, 'Oh, I'd love to do that.' So we got James Taylor."
Taylor, who will perform his signature classic "Sweet Baby James" at Leno's request, said he felt that "Jay's choice of me has a lot to do with his feelings for Massachusetts. He wants to reconnect, since he thinks of himself as a citizen of the commonwealth."
Taylor remembered that he and Leno "crossed paths a couple of times" in Boston during the mid-1970s, appearing at some of the same clubs.
The initial arrangements for tonight's guest appearance (at 11:35 via WNYT, Channel 13, Albany) were made during Taylor's appearance with Leno last fall to promote his "Covers" album. The singer views Leno's late night farewell as "having the element of being a milestone," although "it's not as much of a change as some have thought, since he'll be carrying on at a different time." TV appearances often make Taylor' nervous, he explained, since he prefers to play directly to a live concert audience.
"I think back to the dozens of times I've been on the 'Tonight' show," he said. "But this will be different, since I'm not coming hat in hand to promote something. I have a good feeling about doing this, because I'm there to honor Jay."
After returning from Hollywood and spending some time in the Berkshires, Taylor and his band will embark on a music cruise aboard the Queen Mary 2 late next month, followed by an extensive tour of European festivals.
By late summer, he'll be back in the Berkshires. His Aug. 27-30 extravaganza at Tanglewood includes "Conversations Among Friends with James Taylor" at Ozawa Hall, two Shed performances with guests Yo-Yo Ma and Sheryl Crow, and a Sunday afternoon appearance with the Boston Pops conducted by John Williams.
The events are sold out, but seats may be available through Ticketsforcharity.com, an organization strongly backed by Taylor that offers tickets to concerts and sports events for an additional donation to designated beneficiaries; Taylor selected the Natural Resources Defense Council and the Boston Symphony. He appeared on NBC's "Today" show on Thursday, praising the ticket agency as a superior alternative to "the secondary market."
On Johnny Carson's last show, Bette Midler serenaded him memorably with "One For My Baby"; he became visibly teary-eyed. Taylor may well adapt his lyrics by singing "Sweet Baby Jay." Viewers can expect emotions will be at a high pitch on the "Tonight" set.