June 2nd, 1992, Lemonheads released their fifth album, It’s A Shame About Ray, through Atlantic Records. The Lemonheads’ output is often disregarded or dismissed when discussing the pantheon of great alternative rock albums released during the ’90s. Despite the band’s enormous success, the accolade of serious contenders often evaded them. Maybe it was the perfect, hook-laden, sun-kissed melodies that shunned some. Remember, in the early ’90s, dour introspection and bleak aggression ruled the roost.

Evan Dando’s perfectly sculpted cheekbones, model good looks, and loveable bobblehead persona caused many to write them off even before diving into the music. Either way, the Lemonheads spent all their time not giving a shit about any of that and, instead, focused on writing immaculate, memorable alternative rock songs.

Formed in Boston in 1986, the Lemonheads started life as a snotty punk band. In 1987, they released their debut album, “Hate Your Friends,” on the legendary Taang Records. This was an exhilarating slice of hardcore punk. By album two, 1988’s “Creator,” the band was already beginning to introduce more leftfield influences alongside the Husker Du worship. A smattering of acoustic guitars penetrates the wild abandon. Despite the raucous din, the band knew their way around a melody, even at this early stage.

It was on their third and fourth albums that they found their sound. 1989’s “Lick” saw Evan Dando’s songwriting emerge. While still a raging punk blast, Lick demonstrates why the Lemonheads are such a vital band within the late ’80s and early ’90s alternative rock and punk scenes. Their unique ability to meld the cosmic Americana of Gram Parsons with a vital punk blast of Husker Du and wrap it up in a beautiful two-and-a-half-minute song was impressive.

Released in 1990, “Lovey” is where it all truly came together. Dando took complete control of the band’s artistic vision and vocal duties. On previous albums, lead vocals had been split with Ben Deily. Lovey is the Lemonheads’ first true masterpiece and their first for major label Atlantic Records. It’s an album of vicious intent: serene acoustic balladry and caustic punk rage blend seamlessly in the most natural ways imaginable. Lovely is a remarkable album.

Up to this point, the band had consistently released an album a year from 1987 to 1990. But a two-year gap separated Lovey, and It’s A Shame About Ray. 1992 was a year of landmark releases: Alice In Chains’ Dirt, Stone Temple Pilots’ Core, Screaming Trees’ Sweet Oblivion, L7’s Bricks Are Heavy, and Nirvana’s Incesticide were just some of what poured from the fertile US alternative rock music scene in that landmark year.

Among his contemporaries, Dando’s slacker pop sounds almost Zen. It’s A Shame About Ray’s short songs seem concise and even disciplined. The album has aged incredibly well and plays as something much more complex and contradictory than it may have initially suggested during the heady days of the early ’90s. It’s filled to the brim with exuberant pop melancholy and stays with the listener long after the last notes fade from the speakers.

It’s A Shame About Ray is restless in its pursuit of beauty, mixing gilt-edged pop hooks with country flair and a slashing punk racket. How Dando and Co. get there is irrelevant; for them, beauty is in the eye of the beholder. The band finds it in the grimy edges of punk rock as much as the hook-laden whimsey of an acoustic guitar.

Before recording the album, Dando had toured Australia solo, opening for Fugazi. There, he met Tom Morgan of the band Smudge. They became fast friends and instant collaborators (and are still to this day). Morgan is responsible for co-writing several of the band’s greatest songs with Dando. It’s A Shame About Ray was their first foray into co-writing, producing two songs, including the title track for this release, but more importantly, cementing a lasting artistic relationship.

Dando recalls: “When I returned to Los Angeles (from Australia), I decided I wanted to look after things myself, so I fired my management. I wanted to pick the band up, practice for an hour a day for a month and then make an album, which is exactly what we did.” The album’s subtle genius lies in its devil-may-care attitude. Yet, there’s also a distinct sense that it’s offering a glimpse into a profoundly personal experience.

Opening with the descending guitar riff of “Rockin’ Stroll,” a crashing flurry of tight chord changes races past. Despite its considerable tempo, the song has an infectious bounce and groove. Dando’s warm drawl nonchalantly scrawls across the fevered tempo as a bed of acoustic guitars bristle beneath the electric commotion, adding an irresistible brightness to its one-minute, forty-nine-second runtime.

“Confetti” rolls from the speakers with joyful abandon. Again, the blend of acoustic and electric instruments adds a carefree jangle. Packed with more hooks than most bands can squeeze from an entire album, “Confetti” is a masterclass in ’90s alt-rock, slacker songwriting. It’s a perfect summation of influences from Big Star to Husker Du, The Replacements, Gram Parsons and the cosmic Americana of the Flying Burrito Brothers.

The title track, one of Dando’s best compositions, is most beguiling because of its obtuseness: It could pertain to almost any bad situation, and that ambiguity suggests some tragedy that can’t be named or faced. “It’s A Shame About Ray” was the first single released from the album, with its video garnering heavy rotation on MTV. It features a cameo by Johnny Depp. Dando explains how Depp’s involvement came about, “Winona Ryder was a Lemonheads fan and she made a tape of our songs for Johnny Depp. He liked the stuff and said, “Come and live in my house.”

Dando continued, “We didn’t exactly go and live in his house, but we made the video there, with Johnny in it. It was our first song to chart in the UK. I was under a lot of pressure to deliver hits back then, but I still like that song. We never got the drum beat together or worked on the arrangement, but sometimes the least thought-out songs are the best.” “It’s A Shame About Ray” is a beautifully rendered song, pitch-perfect in tone and delivery; its hazy vision sears into the memory.

“Rudderless” bristles with sophisticated chord structures and an introspective feel that lifts skyward with Julianna Hatfield’s enchanting vocals weaving perfectly between Dando’s pleas. “My Drug Buddy” is a love letter to substance abuse. Wistful and dreamy, its acoustic setting is languid and unrushed, like watching a band perform on a tiny stage through a fog of cigarette smoke as a ceiling fan creates slow-moving vortexes through the air.

“The Turnpike Down” revels on a tripping hook mostly from the ingenious interplay between the drums and guitars. This creative use of rhythmic counterpoint lends the song a distinctive bounce. “Bit Part” opens with Evan’s friend Polly Noonan (also heard at the end of the album Lovey on an answering machine message) screaming in a distinctive accent, “I just want a bit part in your life.” The song is a firecracker romp, clocking in in under two minutes. It’s filled with drama and emotional swagger.

Julianna Hatfield’s bass playing anchors each song with commanding authority throughout the album. But her irresistible backing vocals add another layer of brilliance to the whole record. Julianna, a renowned musical artist in her own right, is one of the keys to this album’s success.

“Alison’s Starting to Happen” tells the story of a girl who finds herself as she discovers punk rock. The song captures the laconic rhythms of suburbia. Dando’s warm, friendly voice gives the songs an emotional resonance. “Hannah & Gabi” is a gorgeous acoustic ballad with shimmering pedal steel guitar played by the legendary Jeff “Skunk” Baxter of Steely Dan and the Doobie Brothers.

“Kitchen”, with its handclaps and effervescent jangle, expertly avoids the pitfalls of becoming twee, instead sounding life-affirming and joyous. “Ceiling Fan In My Spoon” adds menace to its verse before the chorus opens with a light bounce and inventive backing vocals.

“Frank Mills” is a cover of a song from the musical Hair. Featuring just Dando and his acoustic guitar, he sings about meeting a guy named Frank Mills only to lose his address. He asks the listener for help reconnecting them, stating you can recognize Frank by his white helmet and his leather jacket bearing gold chains and the words “Mary,” “Mom”, and “Hell’s Angels.” He and his girlfriend Angela don’t need Frank to repay the two dollars they loaned him; they just want him back. The track is dreamy and humorous. Dando’s easy, unfiltered performance adds a sense of realness, while the casual recording sounds like a single mic there to capture an off-the-cuff moment.

Although “Mrs Robinson” was not originally included on the album’s original pressing, it was subsequently added to future pressings after it became a sleeper hit before It’s A Shame About Ray’s release. The Lemonheads’ version was recorded to celebrate the 25th anniversary of the release of the film The Graduate. The band recorded the song in Berlin while on tour, with Nic Dalton on bass guitar, and released it as a single. Evan Dando later said he “hated” the song and its author, Paul Simon. He noted that Simon intensely disliked the cover, but Garfunkel was more favourable toward it.

With “It’s a Shame About Ray,” the Lemonheads created a masterpiece. Only two years into the ’90s, the album and its title track are among the best releases of the decade (if not beyond). It’s an exquisitely self-contained work of idleness, hunger, and pathos. Since the record’s release, Dando has remained spacey and carefree despite the nihilism that ravaged his Gen X cohorts. He never wanted to be a star. At times, it seems he barely wanted to be a professional musician.

“It’s a Shame About Ray” catapulted the band and Dando into a strange, alien mainstream limelight. At times, it looked as though Dando himself might not survive the decade. Many other outstanding Lemonheads records exist. The band’s back catalogue is rich and vital, but it’s a Shame About Ray is a singular achievement. It perfectly captures a moment in time—a generational marker in the sand.