You can't teach an old Deadhead new songs. John Mayer [ tickets ] found that out the hard way on Thursday (12/29) in San Francisco.

Mayer, a vocalist/guitarist who can thrill an amphitheater full of teenage girls when he is playing his pop material, had a really hard time just keeping the attention of 1,000-or-so Deadheads as he played the blues at the Fillmore.

The crowd members didn't know the material and they didn't want to take the time to learn it. What they wanted was the headliner, Phil Lesh [ tickets ] and Friends, and The Grateful Dead songbook. It's hard to blame them, given how commonplace the John Mayer Trio's performance was on this night.

It was the opening show of a three-night, three-venue New Year's Eve run for the two acts in the City by the Bay. After playing the Fillmore, the pairing moves to the Warfield tonight (12/30) and finishes off the year at the Bill Graham Civic Auditorium on Saturday (12/31). It looked to be an inspired pairing, prompting Rolling Stone magazine to dub the run's finale as one of the 10 top New Year's Eve concerts in the country this year.

Lesh and his newest Friends lineup--vocalist Joan Osborne [ tickets ], guitarist Larry Campbell, drummer John Molo, keyboardist Rob Baracco, pedal-steel player Barry Sless and vocalist/guitarist Ryan Adams [ tickets ]--definitely lived up to their end of the bargain. Unfortunately, Mayer, drummer Steve Jordan and bassist Pino Palladino did not.

What was most troubling about the opener's performance was that Mayer showed absolutely no feel for the audience. When something didn't work, which happened often, the bandleader wouldn't try to change and go another direction. Instead, he would just move ahead stubbornly along the same road.

For instance, Mayer was getting nowhere with his stripped-down, blues-pop numbers. This crowd wanted to dance. It wanted big guitar bits. It wanted noise. So what did Mayer do? He went softer and more intimate and, really, fell on his face and was basically ignored by the crowd.

"Are you having a good time?" Mayer asked the crowd. "That's not a rhetorical question. I just worry."

He had plenty to worry about. For this audience, on this night, Mayer made the wrong step with each new song. He drew heavily from his band's debut, "Try! The John Mayer Trio Live in Concert," and could only muster up lukewarm versions of "Good Love is on the Way," "Vultures" and Jimi Hendrix's "Wait Until Tomorrow." The best thing to come from the stage was spoken, not sung:

"We have a couple of more songs to play," Mayer told the crowd, "then Phil Lesh and Friends are going to come out and show us how it is done."

That's basically what happened. The 65-year-old bassist used his first set to turn back the clock, landing somewhere in early '80s Dead form, and churned out highly inspired versions of fan favorites.

Osborne, who was briefly a member of the post-Garcia Dead, sounded superb as she took center stage for one of the best versions of "Shakedown Street" that I've heard in ages. It was clear from the very start of the show that we were watching the finest Friends roster in many a moon. In all, the music sounded even better than what Bob Weir, Trey Anastasio and other jam-band all-stars delivered back in September at the "Comes a Time - A Celebration of the Music and Spirit of Jerry Garcia" concert at the U.C. Greek Theatre in nearby Berkeley.

Fans were alerted ahead of show time that Osborne was on the bill. But Adams' appearance on the stage was a happy surprise. The vocalist/guitarist—who, between releasing three of his own albums in 2005, still managed to work in a few dates with Phil's Friends--really impressed the crowd on "Friend of the Devil" and "Dire Wolf."

Musically (but not thematically) speaking, the two songs are at the opposite ends of the Dead's spectrum. "Friend of the Devil," as it is traditionally performed in concert, is a slow, mournful number, while "Wolf" is an up-tempo country rocker. It won't surprise anyone who is familiar with Adams' own work to learn that he was able to handle both numbers equally well. (Lesh should sign this guy to a long-term contract.) The set also featured stellar renditions of the classics "Bertha" and "He's Gone."

As good as Phil Lesh and Friends were on Thursday, the band might be even better on Saturday. Mayer is scheduled to join the group for the last set at the Bill Graham Civic, which will also be the first set of 2006. Mayer is a fine vocalist and guitarist. Give him the right material--which, for this crowd, means Dead tunes--and he should do great.