Billy Joel And Happy Gilmore Show Enduring Power Of Gen X And Boomers

ELMONT, NEW YORK – DECEMBER 31: Billy Joel performs during a New Year’s Eve show at UBS Arena on December 31, 2023 in Elmont, New York. (Photo by Myrna M. Suarez/Getty Images)

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The bravura new HBO Max documentary, Billy Joel: And So it Goes, is just the tip of the iceberg in the recently revived cultural centrality of Gen X and even Boomer content icons. If my anecdotal analysis is correct, the Joel doc is resonating in an unusually powerful way among folks often left out of the buzziest current trends. Beyond that, from Pee-wee Herman to Pamela Anderson to Happy Gilmore, we see a lot of enduring power of a number of cultural symbols from decades past.

Challenging Times for the Demos

The Gen X-Boomer alliance hasn’t seemed the focus of the media business for quite some time. Boomers – defined as those born between 1946 and 1964 – have been entirely outside the valued advertising demo of even 25–54-year-olds for 7 years and counting. Gen X, born between 1965 and 1980, is still a part of that cohort but fast leaving the longtime broadcasting demo sweet spot of 18-49.

In terms of mass culture, Gen X and Boomers can often feel on the outside looking in. The theatrical business, especially opening weekends, has been dominated at least since the Marvel Studios’ Iron Man movie in 2008, by superhero films and an array of “sleeper” horror flicks that depend upon far younger audiences for scale. Gen X and Boomer musical acts from The Rolling Stones to U2 to Bruce Springsteen certainly still fill arenas but have a challenging time creating new music that resonates. And as demographic reality sets in, we have seen the passing of cultural legends, with just the last week seeing the loss of Ozzy Osbourne, Hulk Hogan and WKRP in Cincinnati’s Loni Anderson.

The Wonderful World of Documentaries

Then lo and behold, here comes the piano man, or Piano Man if you will. I’ll cop to being a fanatic dating back to seeing Billy Joel perform at Boston’s Symphony Hall, when he couldn’t have come close to selling out Boston Garden. A string of hits has a proud place on what my daughters refer to as “Daddy’s Road Trip Playlist.” And a stack of Billy Joel sheet music sits atop my piano today (for you keyboard artists, take a shot at Prelude/Angry Young Man sometime).

Despite my obvious bias, the Billy Joel documentary is a classic of that genre. You get the deep dives into his creative process and the shifting vicissitudes of the music business for decades. His hit-making success coincided with the explosion of MTV – yeah, some of us can remember when they featured music – so you get a series of memorable music videos. There is the intersection with his ex-wife Christie Brinkley (the “Uptown Girl”), a massive cultural icon in her own right in an era when supermodels dominated the visual landscape. And a series of interviews from Joel’s contemporaries and critics provide a historical positioning for Joel’s music that runs through the great American songbook to the best singer-songwriters of the late 20^th century. And you get a ton of Billy talking about life and music – it’s not all pretty, but it’s pretty real.

Continuing in the Gen X-Boomer doc tableaux we have Pee-wee As Himself, also streaming on HBO Max. In this case, I might have missed the boat the first time around. Certainly, I couldn’t have missed Pee-wee Herman, a ubiquitous pop culture symbol in the 1980s. But I had totally missed the real-life Paul Reubens himself. The recently deceased Reubens was unfairly tagged with various salacious allegations years ago that largely robbed him of years of work at the height of his fame. But the documentary provides a terrific insight into the breadth of his talent, original voice, and widespread influence. He collaborated intensely in the documentary – sometimes to the consternation of its director – and his voice is laced throughout.

Gen X-Boomer Power Everywhere

The Gen X-Boomer influence feels omni-present right now. Who is the most widely “shipped” couple in the celebrity firmament? Liam Neeson (73 years old) and Pamela Anderson (58). My own daughters are asking me – are they really a couple? Just flirting? I’m not sure I care that much, but it sure helps focus your attention on the stars and their film projects. Pamela Anderson is herself a remarkable comeback story, a former Baywatch star who was never taken seriously as an actress in her early days and was in some sense the victim of early viral video fallout (albeit partly self-inflicted). And yet here she is, acclaimed for her performance in The Last Show Girl, and the co-star of one of the buzziest movies of the season, The Naked Gun.

As to The Naked Gun and especially Happy Gilmore 2, both of these new films are driving through the morass of media content with a lot of years on their tire treads. The Naked Gun was released in 1988 and is part of a family of comedy that seems to have passed – the outright silly film, kicked off by Airplane! In fact, in conjunction with Happy Gilmore 2, there might even be a revival of the long-dormant film genre of comedy itself. What was the last really great comedy – Bridesmaids?

The original Happy Gilmore debuted in 1996, and its sequel accumulated nearly 47 million views on its opening weekend on Netflix. Although Adam Sandler, playing the title character, has never gone away in the last 30 years, did you think you’d see a flood of interviews with Christopher McDonald, aka “Shooter McGavin”? Although he’s been on Hacks for years, his cultural cache is once again on course big time.

All of the reflexing of Gen X-Boomer power suggests that there is gold in those marketing hills way beyond the latest TikTok influencer. There is a whole lot of wisdom, experience and buying power ready to tap into if the business is smart about pressing the right buttons.