The 20 Best Grateful Dead Songs of All Time

From gentle acoustic ballads to sprawling psychedelic jams, this catalog stretches from tender folk to full-throttle improvisation. Where do you stand?

1

Truckin'

A 1970 road-life anthem and one of the band's most enduring concert staples.

1000pts

2

Box of Rain

A 1970 ballad written by Phil Lesh for his dying father, closing out American Beauty.

832pts

3

Casey Jones

A 1970 boogie-rock tune about a runaway train, driven by its instantly recognizable riff.

741pts

4

Bertha

A driving 1971 rocker that frequently opened the band's live shows.

706pts

5

Touch of Grey

The band's only top-10 hit, a 1987 anthem of resilience that introduced them to a new generation.

680pts

6

Sugaree

A slow-burning 1972 blues-rock song that became a favorite vehicle for extended jamming.

611pts

7

St. Stephen

A kaleidoscopic 1969 psychedelic song with shifting tempos and cryptic lyrics.

611pts

8

Jack Straw

A 1971 outlaw narrative song known for its shared lead vocals and driving rhythm.

529pts

9

Dark Star

A sprawling psychedelic improvisation from 1968 considered the ultimate vehicle for the band's live jamming.

529pts

10

Ripple

A gentle 1970 acoustic ballad from American Beauty prized for its meditative lyrics.

529pts

11

Fire on the Mountain

A 1978 groove-heavy jam that became the band's signature second-set live pairing.

433pts

12

Scarlet Begonias

A 1974 reggae-inflected tune known for its extended live pairing with 'Fire on the Mountain.'

433pts

13

Sugar Magnolia

An upbeat 1970 love song that became one of the band's most-played live closers.

433pts

14

Friend of the Devil

A 1970 bluegrass-tinged narrative song about a man on the run, a fan-favorite acoustic number.

433pts

15

China Cat Sunflower

A whimsical 1969 psychedelic song often segued live into 'I Know You Rider.'

317pts

16

Uncle John's Band

A 1970 folk-rock singalong that opens the Workingman's Dead album.

176pts

17

Franklin's Tower

A jubilant 1975 jam-band staple built around the refrain 'roll away the dew.'

176pts

18

Estimated Prophet

A 1977 reggae-influenced song written in an unusual 7/4 time signature.

176pts

19

Terrapin Station

An ambitious 1977 multi-part suite blending folklore and orchestration.

176pts

20

Wharf Rat

A 1971 character study of a down-and-out drifter, prized for its emotional peaks in live performance.

176pts