A Long Night with Jimmy Webb

(Jimmy Webb performing at City Winery Boston on November 7, 2026)

Scarcely 24 hours after seeing and hearing Gary Higgins in concert at the Rooted Cafe in the Center for the Arts at the Armory in Somerville, I ventured into Boston to see and hear Jimmy Webb perform at City Winery.

Webb has performed there a number of times, but I have resisted going due to my mixed experiences at the venue particularly with Gilbert O'Sullivan, Leonid and Friends and Wild Taxi. But Webb turned 80 earlier this year and given his status as a songwriter, I figured I might as well go see and hear him before it is too late.

This was my first time at City Winery in nearly a year when I saw and heard Micky Dolenz of The Monkees. That was one of my better experiences at City Winery as was the time I saw and heard Ron Sexsmith and Joan Osborne perform there. 

I was hoping that the evening with Jimmy Webb would turn out to be among my better experiences at City Winery. 

Unfortunately, it turned out to be a long night.

The show was supposed to begin at 7:30 p.m. It started at 7:45 p.m. This would be OK, but it was an opening act named Pete Mancini who had not been billed to perform. He was on stage for all of 15 minutes although he would join Webb on stage towards the latter half of his set. But another half hour passed by before Jimmy Webb finally took the stage.

The best way that I can describe the Jimmy Webb concert is by comparing it to the Gary Higgins concert last night. Higgins played 12 songs over an hour and left people wanting more. It took Webb 2 hours to play 11 songs and people couldn't wait to get out of there including myself. Mind you, this does not account for the numerous people who walked out during the course of the show. While ascending the stairs to leave the venue, I overheard a woman exclaim, "I'm so tired."

This is a shame because there were some interesting stories and some good music. The problem was that Webb did not know how to pace himself and seemed to lose track of where he was in a story. This took the energy out of the room.

Webb began the evening by proclaiming, "Now that freedom of speech has been restored," in reference to Tuesday's elections. While this did go down well with most in the audience here in Blue Massachusetts, I did hear someone seated near me say, "Shut up and sing."

This directive was ignored by Webb who spoke about Stephen Miller's appointment as White House Chief of Staff, praise for soon to be former California Governor Gavin Newsom while reminiscing about how Linda Ronstadt spoke out against George Bush, Sr. at a concert and was booted from the venue. Although it was actually Bush 43 to whom she was objecting rather than Bush 41.

Let me put it this way. I'm sure Gary Higgins' politics are probably fairly similar to that of Jimmy Webb. But Higgins didn't say a word about politics though he sang a song about working people. While I'm sure if Higgins had talked politics, he would have been reasonably received. But some people want to go out and get away from the world for a couple of hours. 

Again, it isn't to say there were a lack of interesting stories. 

There was the story of Webb getting drunk on champagne at the Grammy Awards not expecting to win Song of the Year when his name was announced for the Fifth Dimension's "Up, Up and Away". 

There was the story of Webb begging and pleading with Linda Ronstadt to record his song "Yours for The Taking" and her refusal to let him record his own song on an album of his which she co-produced.

There was his story of Frank Sinatra drinking his father, a Baptist Minister, under the table. 

There was the story of Art Garfunkel calling Webb to ask if he could come to San Francisco and play some songs for him before he chose "All I Know". 

There was also the story of Glen Campbell telling him to get a haircut when they met for the first time despite writing his hit song "By the Time I Get to Phoenix" for him. 

The only problem was it took him an inordinately long time to get from the beginning to the end of his anecdotes. I suppose this shouldn't come entirely as a surprise. On a couple of occasions, I have tried to read his book Tunesmith: Inside the Art of Songwriting. His prose, however, is so dense I just couldn't get through more than a couple of chapters on both attempts before abandoning the book.

Then there is Webb's voice. Now, it should be said that Webb's bread and butter is his songwriting. He is also a superb piano player. His singing voice comes a very distant third. Of course, there are many singers who sing well whose voices diminish with age. Now there are artists who have made a career of not singing particularly well such as Bob Dylan and Kris Kristofferson. Yet their voices draw you into their songs. This is not the case with Webb. Although, to be fair, he can occasionally sum up emotional intensity as he did when he sang "The Moon is a Harsh Mistress", "Wichita Lineman" and "MacArthur Park". Of course, "MacArthur Park" was a hit for actor Richard Harris, someone not known for a prodigious singing voice, but who compensated for it with his theatrical flair.

Webb did offer two salient pieces of advice. 

First, attend a Judy Collins concert before she retires next year. Webb said her voice is as good now as it was when she was 18, but that the death of her husband a couple of years ago has deeply affected her. Collins is scheduled to perform in Lexington, MA later this month, but alas I will be in New York City as I usually am during Thanksgiving week.

Second, contact the Rock 'n Roll Hall of Fame and demand that Johnny Rivers be inducted. This I have done although their AI chat responds, "I cannot help with nomination or induction decisions."

Towards the end of the show, Webb made a point of saying he knows the time will soon come where he will be shuffling off the stage. I don't blame him for wanting to stay in the spotlight as long as he can. Late last month, PBS aired a concert special titled Jimmy Webb: American Songwriter where he is joined by Vince Gill, Lyle Lovett, Ryan Shaw, Sheléa and Andrea Campbell. She is Glenn Campbell's daughter and I had the pleasure of seeing and hearing perform with her Dad on his farewell tour at the Wilbur Theatre in Boston shortly after his Alzheimer's diagnosis in 2012. The PBS special is available for streaming through Thanksgiving.

I'm not sure if I will tune in. As much as I enjoy his songwriting legacy, I think I've had my fill of Jimmy Webb for a while. If Webb can fine tune and retool his live performances, then perhaps he will leave his audiences wanting more.