Grateful Dead Singer’s Best Songs

This song initially appeared as part three of a four-part suite on the Dead’s second album, 1968’s Anthem of the Sun. But while the rest of that sprawling psychedelic vision faded from view soon enough, Weir’s chapter — a rare cowrite with drummer Bill Kreutzmann — stayed a beloved element in their set for many years to come. The line “the heat came round and busted me for smiling on a cloudy day” was based on a true story: “I was arrested for throwing a water balloon at a cop,” Weir recalled in Blair Jackson and David Gans’ 2015 oral history of the Dead, This Is All a Dream We Dreamed. “He was conducting an illegal search on a car belonging to a friend of mine, directly below 710 Ashbury…. I thought this was an illegal search, and it incensed me. Besides, we were having a water balloon fight inside the house at the time.” —Simon Vozick-Levinson

The Grateful Dead wrote the loping “Truckin’” as a group, but Bob Weir claimed the lead vocals, which meant he got to sing one of the defining lyrics of the 20th century: “What a long, strange trip it’s been.”  His rhythm guitar anchors the song’s gloriously shaggy, could-only-be-the-Dead groove, which ambles along like a Robert Crumb character come to musical life. (Which is appropriate, since the chorus borrows from a Crumb cartoon that was, in turn, inspired by a Blind Boy Fuller lyric.) —Brian Hiatt

The Dead performed “Sugar Magnolia” more than 600 times, and with good reason. Co-written with longtime Dead lyricist Robert Hunter, it’s a sunny tribute that Weir penned for his girlfriend Frankie, whom he lived with in the early Seventies. (“Takes the wheel when I’m seeing double/Pays my ticket when I speed” — man, this woman was a saint.) The American Beauty highlight became a joyous anthem for Deadheads, usually the most euphoric moment of any show, and sometimes with a trippy “Sunshine Daydream” coda tacked on (the longer, the jammier, the better). The song also has a memorable moment in Runaway Bride, when Julia Roberts nearly marries the Deadhead, but doesn’t — a mistake on her part. —Angie Martoccio

Robert Hunter’s lyrics imagine a kind of ur-hippie mystic who leaves the straight world behind: “Standing on a tower, world at my command/You just keep on turning while I’m playing in the band.” Weir’s honest vocals saved those words from sounding egotistical — the way he sings it, he’s on an genuine, open-eyed journey. And the music he composed for “Playing in the Band” proved remarkably flexible, as the instrumental break in the middle of the song became the home of some of the Dead’s farthest-traveling jams onstage in the decades after its initial release in 1971. —S.V.L.

Legend has it that John Phillips wrote this rollicking cowboy yarn in a drunken haze circa 1963, so wasted he didn’t even remember composing it. It’s been covered by many, including both Judy Collins and Joni Mitchell, but the definitive rendition belongs to Weir, who made it the single most-performed song of the Dead’s 30-year career. He really made you believe he’d been there in that saloon, sweating bullets at that fateful card game. And he sold the savage twist in the song’s closing lines like no one else could. —S.V.L.

The U.S. blues of a long-haired American kid on the road, trying to hitch a ride, feeling like a stranger in his own country. Weir sings about standing out on the highway with his thumb out, on a cold night, after leaving a broken romance in St. Louis. His only company is the headlights of all the cars and trucks and buses that pass by without picking him up. “Black-Throated Wind” was a highlight of his 1972 solo debut, Ace, with a typically thorny Weir melody and a tale inspired by John Perry Barlow’s experience on a road trip through the South. The Dead played this constantly in 1972, gave it up after 1974, but revived it in 1990 with heavily reworked words. It never sounded windier or lonelier than the definitive 8/2/7/72 version in Veneta, Oregon, in the 100-degree sunshine. —Rob Sheffield

The mournful “Looks Like Rain,” cowritten with Barlow, found Weir saying goodbye to a lover who just left him early one morning. “Run me around and make me hurt again and again,” he sings, “But I’ll still sing you love songs, written in the letters of your name.” With a country-tinged chord progression that jerks around like a gentle panic attack, all while Jerry Garcia’s steel guitar keens and whines around Weir’s voice and Keith Godchaux’s piano plods heavenward, the song was an emotional peak for Weir on Ace. —Kory Grow

The lilting loveliness of this Dead mainstay belies the lyrics, which push it into murder-ballad territory: “Jack Straw from Wichita cut his buddy down,” Weir sings. (The song, never released on a studio album, featured just Weir on lead vocals early on, but he soon started sharing with Jerry Garcia.) Weir wrote the song with Hunter after catching an adaptation of Of Mice and Men on TV. “Hunter had this lyric,” Weir told Uncut. “I grabbed it, and we came with a little sketch of heartland Americana, a ballad about two ne’er-do-wells.” —B.H.

Among the Dead’s best-known guitar melodies is the opening to “Cassidy,” a song Weir wrote with John Barlow that made its debut in the early Seventies. Both a reference to the death of Neil Cassady, a noted figure in the Beat generation, and to birth, it features reflective, spiritual lyrics — “Flight of the seabirds/Scattered like lost words” — through a bright, lifting groove. “Cassidy” was a staple of Weir’s sets in side projects like RatDog and Dead & Company, and its hymn-like characteristics have made the song a multi-generational fan favorite. Its final missive feels all the more relevant today: “Fare thee well now/Let your life proceed by its own design/Nothing to tell now/Let the words be yours, I’m done with mine.” —Shirley Halperin

“My time coming any day,” Weir growls on this apocalyptic reggae stomp, which he wrote with Barlow. Garcia’s bubbling, envelope-filter guitar effect made this Terrapin Station gem groove even harder, a perfect ingredient any time it hit the stage — which happened often. The Dead’s 1977 shows are legendary for a reason, and “Estimated Prophet” is an essential part of them, from Cornell University’s Barton Hall to San Francisco’s Winterland. And when Weir sings “Californiaaaaa!” on the chorus, all that’s left is pure euphoria. —A.M.

“I may be goin’ to hell in a bucket, babe,” Weir sings on this riotous single from 1987’s In the Dark, “but at least I’m enjoyin’ the ride.” The song has an easygoing, circular chord progression, custom-made for bluesy jammy solos, and John Barlow’s lyrics, which were far from progressive, made for a whimsical video that found Weir rolling around zebra-patterned sheets while arguing with a woman he’s trying to set up with a biker and another scene in which he’s riding in the back seat of a convertible with a flute of champagne and a goose in a choker. Weir enjoyed the ride, and the song became a set-list staple. —K.G.