This story is over 5 years old.


We're Gonna Need a Bigger Yacht: One Night with Soft Rock's Holy Trinity

I tried to unpack my hatred of Baby Boomers at a concert featuring Michael McDonald, Kenny Loggins, and Christopher Cross.
Photo by Dustin Downing

Millennial hatred of Boomers is a complicated affair. Though the phenomenon is primarily rooted in an accurate assessment of our selfish elders leaving us in a probable lifelong financial, political, and environmental lurch, there’s undoubtedly some cognitive dissonance and latent youthful rebellion against parents stoking that fire as well. Over the years, my own feelings toward this generation have ossified in nothing short of a smoldering resentment. Not a week goes by where I don’t wonder about the net good the world would experience if the lot of them simply disappeared at once in a Thanos snap. And if you’re a Millennial who hasn’t wondered the same at some point, I can only assume you’re a cop. So, when I was asked to cover a Michael McDonald, Kenny Loggins, and Christopher Cross yacht rock nostalgia show at the historic Hollywood Bowl, a setting that would likely surround me with more Boomers than I’d been around in years, I surprised myself by not only jumping at the opportunity but also by resolving to use the experience to de-escalate my animosity toward these old fucks.


To better accept the boomer, I needed to better understand the boomer, and to better understand the boomer, I would have to become one for the evening. I shaved myself a mustache, put on an outfit I reckoned my dad would wear, replete with tucked in Hawaiian shirt, and set off to the venue. Inside, as I made my way closer and closer to the stage and my press seat, I realized I’d vastly underestimated the homogeneity of this show’s demographics. By the time I’d made it to my seat, the crowd around me was excruciatingly Caucasian and old. Looking toward the even tonier seats, the skin and hair only got whiter. My guest and I were the youngest in spitting distance by at least two decades.

The author gets in "the mood"

This setting was a far cry from the Los Angeles I was accustomed to but, my underestimations notwithstanding, this is exactly what I’d come for. I repressed my impulses of discomfort and judgement and tried to get into a Boomer headspace before Christopher Cross took the stage. I drew inspiration from Danny Glover’s already-iconic “white voice” instruction scene in Sorry to Bother You, borrowing his suggestions to LaKeith Stanfield about speaking like I “don’t have a care in the world” and “got all my bills paid” for my own code-switching that evening.

Christopher Cross took the stage first with an extremely brief set, playing just the hits. As the crowd chanted along to the chorus of “Sailing,” it dawned on me that more than a few of the people around me at this Southern California yacht rock show could be genuine yacht owners.
That this realization hadn’t immediately pissed me off told me that real progress was being made toward stated my goals.


Christopher Cross. Photo by Dustin Downing.

In the brief intermission between Cross and Loggins, I made a run for the concession stands. A surprising number of other Millennials were milling about by the food. I presumed they were all seated up in the nosebleeds. Some wore captain’s hats as if they’d just hopped off a party bus. I scoffed, reassuring myself that my outfit was incomparable to their silly yacht rock costumery. I’d only been a Boomer for an hour and was already turning against the youth. Success?

I returned to my seat as a surprisingly-youthful Loggins took the stage to thunderous applause. As an 80s baby, I’d gone into the concert worried that my surface level familiarity with the trio’s catalogue would leave me unfamiliar and bored at points throughout the show, but just a few songs into his set, it was clear that Loggins, like Cross, would be giving this audience nothing but the comfort food they’d come here for.

With every hit he tossed the crowd’s way, their inhibitions lowered and, before long, bodies that had likely not rocked or swayed in ages were catch the spirit, jerking around like freshly oiled Tin Men. Their rapture was infectious, though. As every vacation-tanned CEO around me earnestly sang along with the “even though we ain’t got money” line from “Danny’s Song” I could tell they actually believed this was the case for themselves. They looked so sweet. For once, I couldn’t find any anger in my heart for their self-mythologizing.


Kenny Loggins. Photo by Dustin Downing.

Loggins closed with a one-two punch of “Footloose” and “Danger Zone” that had the crowd rolling in the aisles in ecstasy. The up-to-this-point dour older gentleman seated next to me finally cracked a smile.

“Heck of a show,” I said to him, offering a verbal olive branch in as best an approximation of my own father’s wording and cadence as I could muster.

“Yes! Good old-fashioned rock and roll,” he replied, before laughing with an actual “ha ha”—a response so perfect that I didn’t once stop to do my usual wondering about what sort of capitalistic evils must have been done to land someone in a seat like his.

Our headliner, Michael McDonald, walked to the stage after an introduction from Thomas Wilkins, who’d been conducting the accompanying house orchestra with aplomb that evening. McDonald wasted no time in proving to the crowd that his pipes were as powerful as his Doobie Brothers heyday. So crisp were the notes in “What a Fool Believes” that they wistfully took me down memory lane, despite the fact that I’d only heard that song for the first time a month before on a podcast.

Michael McDonald. Photo by Dustin Downing.

My kinship with the boomers reached its apogee in a surprise moment during McDonald’s set where he announced he’d be playing “a new one.” In unison, young and old alike, we all quietly groaned and pulled out our phones to check up on missed texts ‘til he got back to the good stuff. Maybe we’re not so different after all. Maybe I should get a braided belt.

The show ended and I left, still in character, skipping the encore for the far more Boomer enticement of being in bed on a Friday night by 11:30 PM. Untucking my shirt on the walk out of the bowl, I felt the first twinges of my return to normalcy. I knew it wouldn’t be long before I was back to my normal justifiably-pissed off, cynical Millennial programming. I’d relished this time, however—a temporary peace treaty brokered by the smooth, breezy tunes of these yacht rock kings—and was in no rush to leap back into the fray of the ongoing generational battle.

Justin Caffier does not own a yacht. Follow him on Twitter.