Jay Leno will conclude his latenight run May 29 by passing the “Tonight Show” baton to final guest Conan O’Brien.

Singer James Taylor will perform on that last episode. And Leno, who spoke to reporters Thursday, said he was planning a surprise “personal” ending.

“I have something unusual and different planned,” Leno said. “It’s something out of left field. It has to do with our show and staff.”

The final week of Leno-hosted “Tonight” episodes will include video packages throughout the week; other guests, previously announced, will include Mel Gibson, Arnold Schwarzenegger, Wanda Sykes and Billy Crystal as well as musical performers Lyle Lovett, Prince and Dwight Yoakam.

Decision to put O’Brien on the couch just three days before “The Tonight Show With Conan O’Brien” debuts reps a contrast to the awkward transition from Johnny Carson to Leno in 1992.

Back then, Carson on his final night opted not to mention Leno. As famously chronicled in the book “The Late Shift,” that angered Leno’s manager at the time, Helen Kushnick, so much that she advised Leno not to mention Carson on his first night.

This time around, Leno characterized the succession as a “peaceful transition of power.”

It’s a very different TV landscape from when Leno took over the show. Carson’s finale attracted around 50 million viewers — while Leno’s first night brought in about 25 million.

Leno said his upcoming 10 p.m. show is still in the planning phases — a set has yet to be built, and beyond the plan to stock the show’s second half with more comedy bits, there’s no format in place yet.

“People like the monologue, they like ‘Headlines’ and some of the bits we do, so we’ll update those,” he said. “The real trick is that second half-hour … the job giving a lead-in to the 11 o’clock news is really important. That’s where our local affiliates make their money. We want to make sure they have a strong lead-in.”

Asked about Boston NBC affiliate WHDH’s attempt to preempt the show with a 10 p.m. newscast, Leno said station owner Ed Ansin’s issues with the network predated him.

“His apprehensions didn’t start with me,” Leno said. “It started a year earlier. NBC has not had a great track record at 10 p.m. He wanted to do a 10 o’clock news in Boston and had been fighting for that long before talk (of Leno at 10 began). We had a nice talk, and we’ll work it out.”

Leno said he believed the competition will be tougher at 10 p.m. and that he’s a “realist” in predicting the show probably won’t beat the competition, at least initially.

“It’s easier to go against a parade of white guys,” he said. “They’re all doing the same thing. … (On the other hand) ‘CSI: Miami’ is the best-looking show on TV. Do I expect to beat them? Probably not.”

Echoing NBC’s take on the 10 p.m. competition, Leno said the show will likely be more successful economically than its scripted competish — and that winning the timeslot would be “gravy.” Plus, once the summer months and repeats are factored in, Leno believes the show “will make up ground and hopefully win.”

Leno also took issue with the criticism that the new 10 p.m. show is forcing out dramas in the hour — and putting scribes out of work.

“There hasn’t been a successful 10 o’clock launch of a drama series in the last five or six years,” he said. “There’s plenty of drama on TV. Look at FX, USA and all of those shows, ‘The Closer.’ There’s more drama now than there’s ever been. What we hopefully will be providing — there’s no laughs at 10 o’clock.”

As for whether advertisers will be willing to pay primetime cost-per-thousand (CPM) rates for the new show, Leno said he believed his show would be much more ad-friendly than the procedural dramas he’ll be up against at 10 p.m.

“If the ratings are there, the ad people will be there,” he said.

NBC Entertainment/Universal Media Studios co-chair Ben Silverman has touted the marketing tie-in possibilities on the new show — but Leno was a bit more cautious about doing too much of that on air.

“Ben is very enthusiastic,” Leno said. “If it were up to Ben, I’d be doing the monologue in a McDonald’s hat and a Budweiser jacket … I’m open to speculation at this point. It will probably be somewhere between Ben’s enthusiasm and ‘no.’ “