Quick Take:

With a jaundiced eye and uncomfortable shoes, Wallace Baine set out to catch “The Sinatra Show” at Chaminade, and though the Ol’ Blue Eyes was generally charisma-free, the atmosphere might’ve been enough to fly him to the moon.

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Yes, I wore the shoes. The ones in the back of the closet that I last wore to a funeral in 2018. They were coated with dust, of course. Historic dust. Tut’s tomb kind of dust. The guy who last wore these shoes was midstream in the Trump years, would have guessed that COVID was — what, an over-the-counter rash cream? A trendy South American fish dish?

I had to drag them outside to get the dust off, to somehow render them something akin to black, their original color. Maybe the power washer could do the trick.

I’m at the stage of life in which shoes must serve a specific musculoskeletal purpose. Cool kicks are for kids. Showy shoes are for showoffs. And these shoes were certainly not made for walking, to paraphrase Nancy Sinatra.

Sinatra! That’s why I have to wear these shoes in the first place — not Nancy, the other one, the scary Sinatra.

We were off to Chaminade Resort and Spa — always a pleasant destination — to catch “The Sinatra Show,” a swank evening of Valentine’s Day good food and swingin’ music, the latter provided by a veteran jazz band called Essence and a young singer named Matt Hall who had the unenviable task of playing Frank, or at least singing his songs.

How does a singer still have the juice to draw crowds 25 years after his death and 70-some years since his heyday? Who can coax regular, sane people to shell out north of $130 from beyond the grave with just a mention of his name — especially in a community famously more David Crosby than Bing Crosby?

To achieve that kind of immortality is something of a magic trick and the list of icons who can pull it off is short — Frank, Elvis, apparently ABBA. Nostalgia is a mighty force in pop culture, but nostalgia alone doesn’t account for Sinatra’s enduring appeal. Like those who fought in World War II or once owned a Packard, those who experienced Sinatra’s golden years are close to the demographic vanishing point. To my cohort (late boomer, early Gen X), Sinatra represented the hostile old guy who called you a punk for leaning on his car. Even for older folks, those now in their 70s and 80s, though they certainly remember Sinatra, for many he was a symbol of what the rock ’n’ roll generation was determined to displace, a menacing right-winger in a tux, worthy of attention only when he tackled cringe-y covers of “Mrs. Robinson” or “Both Sides Now.”

Of course, Sinatra’s classic recordings — the ones that still jump out of the speakers with power and magnetism — can turn around hidebound attitudes, and that’s certainly happened with many younger music fans, including some who showed up at Chaminade last Saturday night.

In my absurdly stiff and creaky shoes, I chatted with a woman as we were all settling into our seats in the ballroom. She professed an abiding love for Sinatra’s music, but, she told me, it was her 17-year-old son who was really gaga for Frank. Say what? Sinatra is reaching into the Post Malone generation? “But,” she told me in reference to her son’s absence, “he didn’t want to come.”

Which gets us right to the nut of what happened at Chaminade last weekend. The teenage Sinatra fan understood what I didn’t. This was never going to be a gathering of Sinatra obsessives, some kind of Ol’ Blue Eyes Comic-con where geeky fans huddle in corners and argue about Frank’s greatest period and who played what on which album. This was a group of people who, on the weekend before Valentine’s Day, just wanted an excuse to wear the best thing they had hanging in the closet, eat some great food, and dance with their partners.

Curtis Reliford (left), a familiar face in downtown Santa Cruz, came out to dance last Saturday at Chaminade.
Curtis Reliford (left), a familiar face in downtown Santa Cruz, came out to dance last Saturday at Chaminade. Credit: Via Tina Baine

In the middle of it all, present on the dance floor almost the entire evening, was one of Santa Cruz’s most familiar faces, Curtis Reliford, the man behind the enormous truck that often (loudly) rolls down Pacific Avenue, advertising peace, love and justice, as well as his philanthropic efforts to raise money for the poor. If you’re like me, you associate Curtis with music. Wherever he goes, music tends to follow (or precede) him. But you’re not going to hear “Strangers in the Night” emanating from his truck. He’s more of a Motown/R&B kind of guy.

Is Curtis a Sinatra fan? Well, kinda. He told me, “I don’t change the channel if I see him on TV.” That’s a bit short of fan-boy zealotry, but it put him in the mainstream here.

What you and I see of Curtis downtown, that he considers his business. Tonight at Chaminade, he’s on his own leisure time. My concession to the romance of the evening was wearing these hellish shoes, but this guy — famous for his red work shirt and overalls — shows up in a cocoa-brown pinstriped suit, complete with snappy fedora. And when you’re dressed like that, you’re not sitting on the sidelines. Curtis danced with about a half-dozen different women over the course of the evening, and though we shared a table, his seat was always empty. He’d appear just to drag away another blushing dance partner.

I saw one man across the room in a hoodie and sandals, which, in this situation, really should constitute at least a misdemeanor. But generally, the crowd was dressed like they were anticipating this evening for weeks, from the always dependably sexy LBD (little black dress) to the Jayne Mansfield-style red spangly gown. Curtis notwithstanding, the men seemed wary of upstaging their wives/girlfriends and kept it kinda golf-tournament casual. The only men in tuxedos I saw were standing on stage.

As far as the music went, the band gamboled through many of Frank’s greatest hits in a professional but largely charisma-free show. I’m fairly certain that the singer was the same species as Frank Sinatra, but the similarities pretty much stopped there.

I asked one Sinatra fan, early on in the evening, what song she really wanted to hear. She mentioned “Summer Wind,” one of Sinatra’s second-tier hits from the 1960s. “Summer Wind” contains a patina of rueful melancholy that I figured would never make it to the setlist at an event like this. Instead we got “Luck Be a Lady,” “Bewitched,” “New York, New York,” “Pennies from Heaven,” and “My Kind of Town” (how easy would it have been to drop in “Santa Cruz” instead of “Chicago” in that tune? Read the room, friend.). Yes, in a show like this, the band could not have gotten away with skipping over “My Way,” and this band dutifully took it on, though it kills the dancing vibe, and it just doesn’t work unless Frank, or somebody equally as trailblazing as Frank, is at the mic. I mean, that’s a song you gotta earn, am I right?

Still, though, the setting was gorgeous, the mood was buoyant, and the dance floor was always jammed. The food, especially the divine desserts, was good enough to make me forget about my shoes for a while. And the evening convinced me that, despite some red-state stereotypes, Santa Cruz is still a place up for a traditional evening of high-fashion fun that doesn’t involve reggae and weed. Yes, there are rooms in Santa Cruz where you could never perform “The Lady is a Tramp,” at least without an accompanying indictment of it from a grad-student spoken-word artist. But here, everybody loved it.

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Wallace reports and writes not only across his familiar areas of deep interest — including arts, entertainment and culture — but also is chronicling for Lookout the challenges the people of Santa Cruz...