“It’s Not My Cross to Bear” (1969)

The first Allman vocal on the first Allmans album starts out perfectly, with a throaty roar. One of the earliest songs he showed to his bandmates (and written when Gregg was in L.A. and hanging out with future members of Poco), this slow-blues declaration of independence from a bad relationship sets the bar high. Sounding wise beyond his years (he was only 22), Allman alternates between toughness and tenderness in the same song.

“Dreams” (1969)

This Allman original was, Gregg has said, the first song of his that his bandmates truly took to. “Let me tell you, they joined right in,” he says of an early rehearsal where he showed them the song. “It was in, brother. They loved it.” The lyrics—”I’m hung up on dreams I’ll never see/Ah, help me baby/Or this surely will be the end of me”—were textbook blues. But from its jazzy feel (partly inspired by Miles Davis) to its swirly, swampy arrangement, this track from The Allman Brothers Band debut also demonstrated Gregg wasn’t a dull traditionalist in any way.

“Whipping Post” (1969)

Not wanting to wake up his sleeping baby, Gregg wrote this landmark early Allmans song on an ironing board in the middle of the night when he couldn’t find any paper. A tortured cry for help, it didn’t start that way, as guitarist Dickey Betts told Allmans biographer Alan Paul: “‘Whipping Post’ was a ballad when Gregg brought it to us. It was a real melancholy, slow blues.” That changed when Oakley worked up that famous intro and the song kicked, and Gregg’s intense, at-the-crossroads delivery puts it over the top.

“Don’t Keep Me Wonderin’” (1970)

From the band’s second album, Idlewild South, this Gregg original extends his writing streak at the time. “Tell me why when the phone rings baby/You’re up and across the floor,” Gregg pleads, answered by his brother Duane’s glorious slide guitar. (OK, there were no cell phones in 1970.) The way Gregg’s voice seems to wander on and off the mic only adds to its power.

“Please Call Home” (1970)

Few capture the pain of watching a lover walk out the door than Gregg does in this downcast Idlewild South ballad: “Take one last look before you leave/Because, oh, somehow it means so much to me.” The song reveals a new level of sophistication in Gregg’s writing as well as in his singing (like the moments of soul-man falsetto). A majestic remake of the song appears on his 1973 solo album Laid Back.

“Statesboro Blues” (1971)

The Allmans’ iconic At Fillmore East album kicks off with his tight, punchy version of Blind Willie McTell’s blues classic, written in the 1920s and referencing Statesboro, Georgia. Gregg rarely sounds so strong and confident, and the traded solos of Duane and Betts landed the song in the Top 10 of Rolling Stone‘s “100 Greatest Guitar Songs.”

“Done Somebody Wrong” (1971)

Another gem from the Allman’s Fillmore set, this Elmore James blues has a joyful swing that allows Gregg the chance to vocally limber up: He alternately exhorts, pleads and brags. Given the impact of his brother Duane’s death soon after these shows, Gregg’s voice wound never quite sounded this burly and firm again.

“One Way Out” (1971)

Recorded during the Fillmore East shows but not released until a year later on Eat a Peach, this rocked-out take on Sonny Boy Williamson’s song shows Gregg turning into a weathered blues man right before our ears.

“Trouble No More” (1971)

Muddy Waters’ Fifties blues hit was another natural fit for Duane’s slide, the Allmans’ dark shuffle, and, especially, Gregg’s ebullient voice. Like “One Way Out,” this Fillmore East cut found a home on the later Eat a Peach.

“Ain’t Wastin’ Time No More” (1972)

“I had that lick for a while, and I remember [Berry] Oakley saying, ‘Man, what is that little thing you keep playing?'” Gregg recalled. Good thing Oakley pushed Allman to finish the song. From the somber opening rumble of Gregg’s piano to Betts’ wistful slide parts, this Eat a Peach gem serves as both an acknowledgement of Duane’s death and a reason for continuing. Gregg said it was partly inspired by “people coming back from the war in Vietnam,” but Duane’s ghost clearly hovers over this haunted but moving song.

“Melissa” (1972)

Dating back to his pre-Allman days in the band 31st of February, “Melissa” was so mellow that Gregg didn’t show it to the Allmans for years; it only resurfaced when the band needed additional songs for Eat a Peach. (Given how much Duane had loved the song, it was also a nod to him.) Yet the combination of strummed acoustic chords and Gregg’s vocal warmth is a natural for the band, making it an immediate Allmans gem. Gregg struggled with a woman’s name for the song until he visited a grocery store and heard a mother yell out to her wandering daughter, “Oh, Melissa, come back!”

“Wasted Words” (1973)

“Can you tell me, tell me, friend, just exactly where I’ve been?” Gregg sings in this opening track from Brothers and Sisters, the first full studio album the band made after Duane’s and Oakley’s deaths. One of the first songs cut for the album, it balances Gregg’s spit-out delivery with the joyful piano of new band member Chuck Leavell.

“Midnight Rider” (1973)

Written in a nearly empty rehearsal hall one night, this Gregg song was first recorded by the Allmans on Idlewild South. But Gregg’s remake on his Laid Back solo album adds new levels of lost-soul catharsis, aided by an expansive orchestrated arrangement. The definition of “haunted” and one of Gregg’s most aching vocals. As Gregg told RS in 1973, talking about Oakley’s death, “It was so hard to get into anything after that second loss. I even caught myself thinking that it’s narrowing down, that maybe I’m next.”

“These Days” (1973)

Many had (and have still) tackled Jackson Browne’s prematurely wise ballad, written when he was a teenager. But no one matched the downcast contemplation in Allman’s version from Laid Back, which also brings out a hint of country balladry to his sound.

“Can’t Lose What You Never Had” (1975)

By 1975, the Allmans were on the verge of collapse and Gregg was increasingly alienated from his bandmates and dependent on drugs to get through it all. That lost-soul murk envelopes this version of Muddy Waters’ song from the Allmans’ Win, Lose or Draw album. Gregg had never sounded so weary or burdened.

“Just Ain’t Easy” (1979)

By the time the Allmans reconvened for the reunion album Enlightened Rogues (one of Duane’s favorite expressions about the band), Gregg had been through the ringer of Cher, the L.A. high life, and fan backlash. Those tortured few years are laid out, if not explicitly, in his finest moment from that album. A dose of morning-after despair, it found Gregg reclaiming the vocal subtlety of his early years.

“I’m No Angel” (1987)

“Good Clean Fun” (1990)

After falling apart again in the 1980s, the Allmans re-formed in 1989 to commemorate their Dreams boxed set. The following year, they made one of their strongest later albums, Seven Turns, with Warren Haynes now occupying the Duane guitar slot alongside Betts. Co-written by Betts and Gregg – the first time they’d penned a song together – “Good Clean Fun” returns the stomp and snarl to their music, and to Gregg’s voice.

“Just Another Rider” (2011)

Produced by T-Bone Burnett, Allman’s 2011 solo album Low Country Blues was yet another unexpected return to form, and its sole original – co-written by Gregg and Haynes – captured the way Gregg could summon up the old evocative power. Sung in a voice deeper and more seen-it-all than ever before, and driven by a horn-imbued arrangement that recalled Laid Back, “Just Another Rider” was an apt, age-aware sequel of sorts to “Midnight Rider”: “Remind you to take it slow/One step at a time, baby.” 

“Who to Believe” (2003)

Gregg summons up his lung power – and his self-doubts and isolation – in this barn-burner from the Allmans’ Hittin’ the Note album. Powered by guitarists Haynes (who co-wrote this song) and Derek Trucks, the band raises hell behind Gregg, who reciprocates in one of his best later-day performances.