# 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?

*By YPB Team · Published August 10, 2026 · https://youpick.best/ranking/the-20-best-grateful-dead-songs-of-all-time*

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## Current results (3 votes)

1. **Truckin'** — 33.33% (1 votes · score 1000/1000)
   A 1970 road-life anthem and one of the band's most enduring concert staples.
2. **Box of Rain** — 33.33% (1 votes · score 832/1000)
   A 1970 ballad written by Phil Lesh for his dying father, closing out American Beauty.
3. **Casey Jones** — 0% (0 votes · score 741/1000)
   A 1970 boogie-rock tune about a runaway train, driven by its instantly recognizable riff.
4. **Bertha** — 33.33% (1 votes · score 706/1000)
   A driving 1971 rocker that frequently opened the band's live shows.
5. **Touch of Grey** — 0% (0 votes · score 680/1000)
   The band's only top-10 hit, a 1987 anthem of resilience that introduced them to a new generation.
6. **Sugaree** — 0% (0 votes · score 611/1000)
   A slow-burning 1972 blues-rock song that became a favorite vehicle for extended jamming.
7. **St. Stephen** — 0% (0 votes · score 611/1000)
   A kaleidoscopic 1969 psychedelic song with shifting tempos and cryptic lyrics.
8. **Jack Straw** — 0% (0 votes · score 529/1000)
   A 1971 outlaw narrative song known for its shared lead vocals and driving rhythm.
9. **Dark Star** — 0% (0 votes · score 529/1000)
   A sprawling psychedelic improvisation from 1968 considered the ultimate vehicle for the band's live jamming.
10. **Ripple** — 0% (0 votes · score 529/1000)
   A gentle 1970 acoustic ballad from American Beauty prized for its meditative lyrics.
11. **Fire on the Mountain** — 0% (0 votes · score 433/1000)
   A 1978 groove-heavy jam that became the band's signature second-set live pairing.
12. **Scarlet Begonias** — 0% (0 votes · score 433/1000)
   A 1974 reggae-inflected tune known for its extended live pairing with 'Fire on the Mountain.'
13. **Sugar Magnolia** — 0% (0 votes · score 433/1000)
   An upbeat 1970 love song that became one of the band's most-played live closers.
14. **Friend of the Devil** — 0% (0 votes · score 433/1000)
   A 1970 bluegrass-tinged narrative song about a man on the run, a fan-favorite acoustic number.
15. **China Cat Sunflower** — 0% (0 votes · score 317/1000)
   A whimsical 1969 psychedelic song often segued live into 'I Know You Rider.'
16. **Uncle John's Band** — 0% (0 votes · score 176/1000)
   A 1970 folk-rock singalong that opens the Workingman's Dead album.
17. **Franklin's Tower** — 0% (0 votes · score 176/1000)
   A jubilant 1975 jam-band staple built around the refrain 'roll away the dew.'
18. **Estimated Prophet** — 0% (0 votes · score 176/1000)
   A 1977 reggae-influenced song written in an unusual 7/4 time signature.
19. **Terrapin Station** — 0% (0 votes · score 176/1000)
   An ambitious 1977 multi-part suite blending folklore and orchestration.
20. **Wharf Rat** — 0% (0 votes · score 176/1000)
   A 1971 character study of a down-and-out drifter, prized for its emotional peaks in live performance.

Tags: music, rock, bands, grateful dead