Dead in December: 9 Bluegrass Covers of Grateful Dead Classics

It’s certainly true that the Grateful Dead were never a bluegrass band, starting with the fact that their lineup had not just one drummer, but two. And yet it also can’t be denied that the group’s musical DNA has a wide streak of bluegrass deep within, both in terms of licks and improvisational flair.

In large part, that’s due to the late Jerry Garcia – “Captain Trips” – who started out as a banjo player before finding his most famous calling as the Grateful Dead’s lead guitarist. Before that, Garcia played in folk circles for years, and his many extracurricular collaborators included David Grisman, Peter Rowan, Don Reno, Chubby Wise and other titans of the genre. More than a quarter-century before O Brother, Where Art Thou? took bluegrass to the top of the charts, Garcia’s 1973 side project, Old & In the Way, stood as the top-selling bluegrass album of all time.

Garcia and the Dead’s bluegrass bona fides are solid indeed, as shown by artifacts like the Pickin’ on the Grateful Dead series (not to mention Grass Is Dead, a tribute act). But maybe the strongest testament to the strength of the Dead’s bluegrass-adjacent side is what other artists have made of their catalog. Countless bluegrass musicians have covered Dead songs in ways that would appeal to even the staunchest chair-snapping purists. Here are some of the best.

“Friend of the Devil” – The Travelin’ McCourys (2019)

This rounder’s tale is the granddaddy of ’em all, a bluegrass staple from almost the moment it appeared on the Dead’s 1970 proto-Americana classic, American Beauty. Long a picking-circle staple at festivals, it’s been covered by everybody from Tony Rice to Elvis Costello. But here is a fantastic cover by one of the finest family bands in all of bluegrass, captured onstage at the Grey Fox Bluegrass Festival in 2019. In contrast to the manic pace of the original, this version proceeds at more of an elegant glide. But it’s still got plenty of get-up-and-go, with killer solos over walking bass and a great Ronnie McCoury lead vocal.

“Dire Wolf” – Molly Tuttle (2022)

Among the most acclaimed young artists in bluegrass, Molly Tuttle is a two-time Guitar Player of the Year winner from the International Bluegrass Music Association. She also won IBMA’s Album of the Year trophy for 2022’s Crooked Tree, which included the 1970 Workingman’s Dead standard “Dire Wolf” as a bonus track. Equal parts folk fable and murder ballad, it’s something like “Little Red Riding Hood” with an unhappy ending. And Tuttle’s vocal is even more striking than her guitar-playing.

“Wharf Rat” – Billy Strings (2020)

Possibly even more acclaimed as a guitarist is William “Billy Strings” Apostol, another IBMA Awards fixture (and multiple Entertainer of the Year winner) who is frequently likened to Doc Watson. But few guitarists have ever conjured up Garcia’s sound, spirit, and all-around vibe as effectively as Strings. A song about a lost soul in a seaside town, “Wharf Rat” first came out on the Dead’s eponymous 1971 live album. Strings’ 2020 live version from the Capitol Theatre in Port Chester, New York, is amazing, as Strings doesn’t sing it so much as inhabit it. The money shot is his guitar solo that begins just after the five-minute mark.

“Scarlet Begonias” – The Infamous Stringdusters (2020)

Gambling is one of the Dead’s recurrent tropes and “Scarlet Begonias” gives it a playful spin with a loping guitar riff. The original dates back to 1974’s From the Mars Hotel and it’s been widely covered in oddball styles by the likes of electronic duo Thievery Corporation and the ska band Sublime. But “Scarlet Begonias” has never had it so well as in this excellent bluegrass version by The Infamous Stringdusters, shot onstage at Seattle’s Showbox just ahead of the pandemic in early 2020.

“Ripple” – Dale Ann Bradley (2019)

More often than not, vocals tended to be the Dead’s weak link. But that is not a problem for Kentucky Music Hall of Famer and five-time IBMA Female Vocalist of the Year Dale Ann Bradley. The elegiac “Ripple” began life as the B-side to the “Truckin’” single and was also a show-stopper on the Dead’s 1981 acoustic live album, Reckoning. Bradley covered it on her 2019 LP, The Hard Way, with Tina Adair providing truly lovely vocal harmonies.

“Uncle John’s Band” – Fireside Collective (2022)

One of the Dead’s folksiest numbers, “Uncle John’s Band” kicked off Workingman’s Dead at an easy-going amble – a clear departure from the psychedelic excursions of the Dead’s earliest work. This live version by the young Asheville, North Carolina, band Fireside Collective reimagines “Uncle John’s Band” as sprawling jam-band fodder.

“Cassidy” – Greensky Bluegrass (2007)

“Cassidy” first appeared on-record as a Bob Weir solo tune on his 1972 side-project album, Ace, but it’s been on multiple Dead live albums over the years. It’s always been something of an enigma, inspired by a young girl as well as Neal Cassady. Michigan jamgrass ensemble Greensky Bluegrass gets to its beat-poet heart on this version from 2007’s Live at Bell’s.

“Tennessee Jed” – Front Country (2018)

A frequent theme for the Dead was being in motion, whether traveling toward something or running away from it. So it follows that homesickness would be an aspect of their music, perhaps most overtly on this wistful song from the double-live LP, Europe ’72. California’s Front Country put “Tennessee Jed” through its paces in this 2018 version from their “Kitchen Covers” series.

“Touch of Grey” – Love Canon (2014)

If the Dead wasn’t a bluegrass band, they most definitely weren’t a pop band, either. But the group had occasional brushes with the Hot 100, most famously with the 1970 statement of purpose “Truckin’” and its “what a long strange trip it’s been” tagline (even though the group had only been together about five years by then). “Truckin’” stalled out at No. 64 and was later eclipsed by its 1987 sequel “Touch of Grey” – an actual Top 10 hit with its bittersweet conclusion, “We will get by, we will survive.”

From Charlottesville, Virginia, Love Canon strips away the ’80s pop keyboards and covers the song well as straight-up bluegrass on 2014’s “Dead Covers Project.”

Photo Credit: Old & In the Way, courtesy of Acoustic Disc.