In the mid-80s my father and his neighborhood friends assembled a slow pitch softball team called “R Gang.” Most of the dads were firmly middle-aged or fast approaching the turn. Several owned Porsches. I was a wide-eyed tween at the time of the their first official practice — still fairly convinced that my father was a superhero and that his friends were minimally powerful, and possibly much more. At that practice, I saw some of the guys launch fly balls deep into the power alleys. I saw them turn a couple of double plays. And I saw them field some routine grounders and make the throws over to first look pretty easy. It wasn’t much, but I’d seen enough. I was convinced of their greatness. 

That weekend, I returned to the same field to watch R-Gang play against the local Police Department team. R-Gang lost 20 to 1. I think the only run they scored was through a walk and a couple of pathetic bunts. R-Gang committed more errors than the scoreboard could reflect and the police team’s worst player hit the ball twice as far as R-Gang’s best player. By the bottom of the sixth inning, I was completely confused and slightly humiliated. As I stared bewildered at R-Gang in the field, all I could see was paunch, sweat and male pattern baldness. These men who were the giants of my neighborhood were suddenly just men. Middle-aged men. They all had their talents. One was an exceptional dentist. One was apparently a great textile merchant. But, deep down, they were just guys, looking at fewer tomorrows than yesterdays. It was an eviscerating revelation -- one that would go unrivaled until several years later, when I saw The Traveling Wilburys’ video for “Handle with Care” on MTV.

In 1988, Bob Dylan was in a rut. His previous two albums, “Down in the Groove” and “Knocked Out Loaded,” were critically ravaged. He’d taken to wearing sequined jackets in concert. There were loud whispers that maybe he’d “lost it.” Meanwhile, Tom Petty was on a bit of a cold streak, himself. After the success of “Southern Accents,” “Let Me Up (I’ve Had Enough)” was perceived as a step in the wrong direction. In 1987, temporarily out of great ideas, the two men -- Dylan and Petty -- licked their wounds on tour together, The Heartbreakers backing Dylan. 

Roy Orbison and George Harrison could relate. For most of the early 80s, they’d been in career purgatory. Roy appeared tragically cursed and George seemed mindfully indifferent to commerce. However, in the back half of the decade, both experienced unexpected revivals thanks, in large part, to Jeff Lynne. Though he could still craft the occasional hit for ELO, Lynne had started to flex as a super-producer. He was functionally the precursor to Rick Rubin -- celebrating beloved heritage acts with white glove services. But whereas Rubin pored over every single instrument, Lynne would lacquer songs with honey dipped hooks and strings. Orbison, who’d been in a creative cave before David Lynch pulled him into “Twin Peaks,” still had the sort of range and vibrato that paired nicely with Lynne’s sweeping gestures.

Harrison’s comeback, though, was both greater and more widely celebrated. Since “All Those Years Ago,” in 1981, the Beatle had not so much as sniffed the Pop charts. It seemed, in fact, that he was intentionally skipping work. Everything changed, however, in 1987, with "Got My Mind Set on You.” Whereas George had recently seemed interested only in domestic or existential pursuits, momentum shifted with “Cloud Nine,” an album produced and significantly performed by Lynne. Not only was George writing and recording again, he began to talk about assembling a new group. And not just any group, but a “supergroup” of friends. So, when his label asked for a B-side for “This Is Love,” he and Lynne sent out the signal. Dylan, Petty and Orbison responded and descended upon Los Angeles to record “Handle With Care.” The occasion was immediately and evidently too wonderful to simply be a one off. And so, five of the most important musicians in the history of Rock and Roll -- a Beatle riding a hot streak, a Poet Laureate who’d lost his muse, a giddy super-producer, a member of Sun Records inaugural class, and the not yet forty-something acolyte  -- became the Traveling Wilburys.

The Traveling Wilburys would go on to become the most legendary inside joke slash mutual admiration society in the history of popular music. There had been “Rock Supergroups” before -- The Yardbirds, Cream, Blind Faith, Derek and the Dominos (seemingly anything Clapton related), but none had been assembled in middle age. In time, the Wilburys would set the template for The Notting Hillbillies, Little Village, Hindu Love Gods and Dave Grohl’s entire career. But, in 1988, they were completely novel. Their first album, hopefully titled “Traveling Wilburys Vol. 1,” was a Harrison, Lynne and Orbison-forward, Skiffle record. Petty was there in an important, but supporting, role. Dylan hosted the group at his house, helping with food services and contributing a few songs, including the enduring, Springsteeny semi-hit, “Tweeter and the Monkey Man.” But, this was George and Roy’s album, decorated and wrapped by Lynne. “End of the Line” and “Handle with Care” were both major Pop hits, delighting fans with the sweet loveliness of two voices sticking to the sandpaper of the two other voices. The album sold millions of copies and inserted itself into heavy rotation on MTV, alongside Guns N’ Roses and Paula Abdul.  

Other than its title, “Vol. 1” appeared in every way to be a too good to be true, once in a lifetime hang. The music succeeded, in part, because of the weight of the players, but also because of its offhanded, casual charm. There’s a lot of jangle. The harmonies are endearing, but would never be confused for The Beatles. And there is only one song that stretched past four minutes. As an event, it felt important. But as music, it sounded anything but. The album wasn’t epic. It was simply...fun.

Even as a newly minted teenager, however, I understood that it was not the signifier of the Wilburys that mattered. The songs were offhandedly very good — yes. But, more importantly, they signified something about middle age. About growing older and knowing that the hourglass has turned over. With the exception of Petty, all of the band members had age appropriate mullets and belly fat. And Tom, who always bordered on gaunt, looked more like a skeleton troubadour than a young rock god. The quintet didn’t look exactly like my dad’s softball team buddies. But, if you just squinted at their shape and color, they were close enough.

Collectively, they represented a generational pivot. The Wilburys were Boomer heroes turning from the corner of vim and vigor towards the intersection of casual and playful. It was five men advertising their past prime status. It was the commodification of a collective second half. There were still big ideas. Justice mattered. So did the environment. And love was still going to save us. But, along the way, couldn’t we all just kick back, laugh, sing and make a few bucks? Apparently, if Bob and George said so, then the question was rhetorical. The Traveling Wilburys confirmed that the already thin line between Hippies and Yuppies had been permanently erased. 

Less than two months after their debut album was released, Roy Orbison died of a heart attack. Though I probably thought that he was seventy years old and, in my defense, he looked nearly that age, Orbison was only fifty two at the time. With his loss, The Wilburys' victory lap became doubly resonant. “Vol. 1” was no longer simply a middle age celebration of enduring friendships. It became a eulogy -- a tribute. It was also a creative watershed for Dylan and Petty. In the two years that followed, Tom would work with Lynne again for “Full Moon Fever,” the best selling album of his career. Meanwhile, Dylan found inspiration in a new partnership with Daniel Lanois, and dug himself out of his critical and commercial quagmire with “Oh Mercy.” It seems unthinkable that either new direction would have occurred without the Wilburys.

While their debut is a fondly remembered, possibly iconic, musical event, the Wilburys’ second (and final) album has been virtually forgotten by history. In fact, for many years both records were out of print, the former preserved only by its legacy on Classic Rock radio. But -- yes -- there was a second coming. In 1990, having sufficiently mourned and gone their separate ways, the supergroup reunited. Part of the impetus must have been the joy of making music together, among friends. Part may have been a desire to honor Orbison. And part may have been unfinished business from the original sessions. Underlying it all, however, was George. After two decades without a band, Harrison obviously liked playing a part in an ensemble again. Additionally, he’d not toured in many years and so, the allure of a Wilburys’ tour hung in the air as a wildly lucrative possibility. Whatever the root cause -- love or money or both -- the band ambled back into the studio in 1990, without their beautiful, doomed elder statesman. In the fall of that year, “Traveling Wilburys Vol. 3.” was released. The bad “dad joke” title (which was proposed by George) suggested a lost, second volume which, of course, never existed. 

Without Orbison floating through the notes, the Wilburys’ sound shifted. There was a certain symmetry in pairing Harrison and Lynne (who sang like a lesser Beatle) against Dylan and Petty (who sang like a lesser Dylan). The smooth against rough dynamic still worked, just without the dark reverie of Orbison’s tenor. Additionally, Dylan, who was somewhat quiet on the debut, came to the fore on “Vol. 3.” As the new patron saint of the group, his style and voice are the dominant force of the record. And while the album does still generally stick with Buddy Holly Pop, Rockabilly and early 60s Rock and Roll, there is a looseness about it that is more Dylanesque than Lynnesque. If “Vol. 1” was Jeff Lynne reimagining the “Sun Sessions,” then “Vol. 3” is more like Lynne touching up “The Basement Tapes.” These are songs designed to delight the band much more than the market. 

“Vol. 3” opens with greater force, if less melody, than its predecessor. In fact, the guitars on “She’s My Baby” have more in common with Nirvana than ELO. The four singers trade verses and inside jokes on a song that feels, in part, like a throwaway and, in part, like their favorite track on the record. Curiously, there is nothing else quite so heavy on the album. By track two, “Inside Out,” they turn towards a style that would be canonized by Tom Petty and The Heartbreakers’ on “Into the Great Wide Open.” It’s light and comfortable, with the hook cleaned up, pushed forward and garnished with a little of George’s syrupy vocals. 

Soon after its confident start, however, “Vol. 3” gets a little lost. There are a couple of early Rock throwback numbers -- “Seven Deadly Sins” and “New Blue Moon” -- that sound like regular guys sending up late 50s R&B or Rockabilly. At their worst — with the extra doses of sax and the middling tempos — they even begin to resemble Sha Na Na. The fact that the Wilburys had unmatched resumes adds some irony to informality of the affair, but does not rescue the fate of every song. When the songs miss, they don’t sound like unfinished sketches or unpolished gems. They sound like middle aged guys remembering the music of their youth, but unable to access the excitement of it.

There are, of course, wonderful moments. “Where Were You Last Night” is typically retro, but tender in a way that the Sock Hop numbers are not. It’s just a simple R&B song that pits Dylan’s smoke and glass vocals against the sweetness of George’s voice. It’s not much, but what it is definitely lands. Elsewhere, the men get to take off the uniform and just be themselves: Jeff adds strings, George adds sitar and Bob tells wild tales. And these personal touches, of course, have their charms. But, overall, the album lacks the cogency of their debut. “Cool Dry Place” is Petty joking about how messy Dylan’s home studio is while “Poor House” is honest to goodness Cowpunk. The former is cute and the latter interesting, but neither are essential. The push pull between Lynne’s instincts and Dylan’s experimentalism, though, produced less even results. On the other hand, Lynne’s style, while sometimes formulaic and limiting, was undeniably effective for Petty

While the middle of the album struggles to find its way, the band does eventually gather itself. “You Took My Breath Away” features Petty on lead, with Lynne at the dials, channeling Roy Orbison. It’s plainly romantic, with just a little slide guitar and Tom’s too easy one liners getting to the heart of the matter. In many ways, it forms the mold that would produce “Full Moon Fever.” It also recalls “The Caruso of Rock” and, inasmuch, could have served as a perfectly sweet closer for the album. Unfortunately, the band instead opted to get silly one more time for “Wilbury Twist.” The novelty song is exactly what you’d expect -- sloppy and amusing. It made for an entertaining video, but not much more.

Less than forty minutes after “Vol. 3” began and less than two years after they first surprised the world, the Traveling Wilburys were gone. There was no world tour. They never went back and recorded “Vol. 2.” In fact, George basically stopped recording altogether, having apparently lost his muse as quickly as he’d relocated it. For most of the 1990s and early 2000s, both albums were out of print. Casual fans quickly forgot about the second record, in particular, and, it seemed, George might have as well. Dylan, meanwhile, was creatively reborn, embarking on a sixth or seventh phase wherein he delved into traditional Folk and Blues. And Petty Petty became the biggest Rock star in the world, bridging the gap between Boomers and their Gen X children.

There were, of course, eventual reissues of the Wilburys’ albums as well as a commemorative box set. Looking back now thirty plus years later, though, it’s not the music that has specifically endured. A couple of songs still sparkle and a few others are close behind. However, their import mostly lies in what they represented for us: Settling down and taking it a bit easier. The joy of camaraderie, even (especially) in middle age. The possibility of great second halves. But also the honor in just hanging things up and staying at home. The Wilburys were a “supergroup” in name only. In reality, they were probably only a “very-good-group.” But they were a swan song for George and Roy and a well of inspiration for Bob and Tom, when they desperately needed it. For Jeff, they were a once in a lifetime job. They did something that superstars rarely get to do. They made two albums, at home, unencumbered by the industry, with zero downside and all of the benefits of friendship. They were the slow pitch softball team that was unconcerned with winning or losing. Either way, there’d be beers after the game.

by Matty Wishnow