Home » Playlists » Top 18 Best Grateful Dead Songs of All Time

Top 18 Best Grateful Dead Songs of All Time

These days, Palo Alto, California, might be better known for tech companies. But it was also home to one of the most legendary bands of all time – the Grateful Dead. This is a band that helped to define the 1960s counterculture and psychedelia. This is a band that invented their own sub-genre of music – jam rock. And this is a band that toured incessantly for 30 years.

But what are the best Grateful Dead songs of all time? This isn’t a band that ever got a lot of radio play, and they only ever had one top 40 hit, so it’s pretty subjective. Instead, I’ll look at the most loved, most played songs that this legendary group put out over their incredible multi-decade run.

The Grateful Dead: Bio

Best Grateful Dead Songs of All Time

Just who were the Dead, and why were they so happy about it, anyway?

The band, originally called the Warlocks, was formed in Palo Alto in 1965 by Jerry Garcia (lead guitar, vocals), Bob Weir (rhythm guitar, vocals), Ron McKernan (keyboards, vocals, harmonica), Phil Lesh (bass, vocals), and Bill Kreutzmann (drums). In 1967, the founders were joined by a second drummer, Mickey Hart, and lyricist Robert Hunter.

They also toured and recorded with numerous other musicians over their incredibly long stint.

This was a band like no other…

From the beginning of their career to the end, they played music of all different styles – rock, jazz, blues, country, pop – refusing to be pigeonholed. They played as the house band for massive acid tests and hippie meet-ups. They held free concerts and supported their fans when needed, helping to build a massive community of dedicated “deadheads.”

The band had their music released on over 200 albums, mostly live recordings made by themselves and their fans. And they continued to jam and rock live until 1995 with the death of Jerry Garcia. What a long, strange trip it must have been.

The Greatest Grateful Dead Songs

With a band like this, choosing their best songs is no easy feat. They not only played hundreds of songs over their career but they also rarely, if ever, played a song the same way twice. But so many of their songs are beloved even if they were never even recorded in the studio. In this list, I’m going to take a look at the songs that got the most attention and the most play in concerts.

Top 18 Best Grateful Dead Songs of All Time

Dark Star

Dark Star” is a single released in 1968 and later recorded on the 1969 Live/Dead album. This track is aptly named with its other-worldly, sparse instrumentation. It’s more of a sonic experiment than a song, and truly demonstrates the psychedelic sound that the Dead were later known for.

The music was Jerry Garcia’s, while the lyrics were written by Robert Hunter. He came up with the chorus by re-wording lines from the T.S. Elliot poem The Love Song of J. Alfred Prufock. Heavy.

Uncle John’s Band

This is one of the Dead’s songs that most people know. It was written by Jerry Garcia and lyricist Robert Hunter in 1969. The band added it to their concert rotation first, and then later recorded a version for their 1970 album Workingman’s Dead.

This is a classic acoustic song that really gives a sense of the original Dead sound. It features groovy percussion sounds and close harmony singing for a really chilled-out, folksy vibe. To me, this is a hippie freak out in the park kind of song for sure.

Box of Rain

Phil Lesh was classically trained as a trumpeter before taking over bass duty for the Dead. He rarely sang lead, but “Box of Rain” from 1970s American Beauty is one of the few songs where he took center stage. After all, this country/folk song was written by him together with Robert Hunter.

The Deadheads would yell out “Let Phil sing!” to request the song in a good-natured jibe at the band in their live concerts. But this song was also pretty heavy as well. Lesh wrote it for his father, who was dying of cancer, telling him, “A box of rain will ease the pain / And love will see you through.”

Truckin’

Now, if you’re looking for a blues-rock song that’s one of the best songs ever to drive to, “Truckin’” is it. This 1970 hit is definitely one of the best-known Dead songs and got a lot of attention and airplay back in the day.

It has that Americana country twang, bluesy keyboards, and a swing that keeps the track driving along and you driving along, too! While it may seem simple and sing-alongy, listen closely – the interplay of the guitars is pure genius here!

Ripple

The B-side to “Truckin’” is also one of the Grateful Dead’s most beloved songs. “Ripple” has a slow, old-timey country/gospel feel like a hymn of sorts.

This song was written by Robert Hunter, reputedly on a drunken afternoon songwriting binge in London. The lyrics are mystical and spiritual, though it’s not clearly a religious song. The tune was written by Jerry Garcia, and it was recorded in 1970 to join “Truckin’” on one of the Dead’s most popular single records.

Sugar Magnolia

Sugar Magnolia” is another track from 1970s American Beauty that became one of the Grateful Dead’s best known songs. This song was written by Bob Weir and Robert Hunter, and it’s Bob who always sang the song live. “Sugar Mag” is a lovely, floaty song about nature and love and is basically the whole flower power movement distilled into a single song.

Casey Jones

Even if you’re not a huge Deadhead, you’ll probably immediately recognize the opening lines to 1970s “Casey Jones.”

“Drivin’ that train / High on cocaine.”

The Dead were no strangers to drugs and sang about them in many of their songs. This was another Garcia/Hunter collaboration that really worked out great. It has a fun and memorable chorus, and the music has a solid groove that you can really get down to. Apparently, Casey Jones was a real train engineer, but I have no idea if he really sped around drug-fueled or not!

Friend of the Devil

For “Friend of the Devil,” the powerhouse duo of Garcia and Hunter was joined by country-rock singer-songwriter John Dawson, and you can really hear the country influence here. This track came out on 1970s American Beauty and is another real slice of Americana. The guitar riff here is twangy and as memorable as anything else the Dead recorded, and the unusually straightforward lyrics invite a fun sing-along.

Bertha

Moving on with my thoughts on the Best Grateful Dead Songs of All Time, in 1971, the Dead released their second double-live album. It was self-titled because the label rejected their original title, Skull F*ck, and is now known by fans as the Skull & Roses album because of the cover art.

“Bertha” is a classic track from that album that became a fan favorite. It has a strong groovy rock driving rhythm and is one of the band’s fastest tracks. Lesh’s bass line is really the star here, bouncing around and pushing the song forward while providing a great counterpoint for Garcia’s guitar diddling.

Playing In The Band

Also, from the 1971 Skull & Roses album, “Playing In The Band” was one of the Dead’s bigger hits. It got a fair bit of attention and radio play because darn it, it’s just a great song!

This is another Bob song with help from Robert Hunter and Mickey Hart. It has a cool, southern rock/country feel very reminiscent of CCR, and that may be a big part of why it got radio play. But it also features something unique – a 10/4 time signature essentially unheard of in popular music.

This song also has the title of longest ever Dead song – they once played it live in 1974 for an incredible 46 minutes. Now that’s a jam!

The Wheel

This song was actually recorded originally as part of Jerry Garcia’s first solo album, Garcia, in 1972. However, it quickly became a part of the Dead’s canon and was played live all over the place.

It featured Jerry Garcia singing with Bill Kreutzman on the piano. Talk about a catchy tune, alright. The chorus comes back around like a wheel, repeating rotating imagery to great effect. And the singing pedal steel guitar work here makes it a real piece of Americana.

China Cat Sunflower

The weird and wonderfully named “China Cat Sunflower” was written by Garcia and Hunter and released on the 3rd Dead studio album, 1973’s unpronounceable Aoxomoxoa.

The strange lyrics are appropriately trippy, but it’s the guitar work that really sets this track apart. Jerry Garcia and Bob Weir pay diddly riffs back and forth off one another throughout the whole song, creating at once a guitar battle and a harmonious counterpoint that’s mesmerizing. Through in Lesh’s bass, and you’ve got one of the most beautifully interwoven Dead songs ever.

I Know You Rider

It became a concert standard to play “I Know You Rider” back to back with China Cat Sunflower as a sort of medley. As the second half, “I Know You Rider” was a bit more powerful and driving.

This is a song that was actually a traditional blues song with roots in the deep early beginnings of blues. But it was adapted by the Dead and worked into one of their great jam songs. It has simple lyrics for a Dead song, and that leaves a lot more focus on the music – this is actually one of the Grateful Dead’s most powerful rockers!

Eyes of the World

Next in my rundown of the Best Grateful Dead Songs of All Time, the 1973 studio album Wake of The Flood brought the band into some new musical directions, like blues, R&B, and jazz-rock. “Eyes of the World” definitely fit into the last category. And although it was only a five minute track on that album, it soon morphed into a 15-20 minute jam session when played live.

It has a slightly swinging feel with music by Jerry Garcia. And the lyrics are some of Robert Hunter’s best and most deeply poetic. He encourages you to “Wake up to find out that you are the eyes of the world.”

Stella Blue

Another memorable track from 1973’s Wake of The Flood is “Stella Blue.” This is yet another Garcia/Hunter joint and one of the band’s softest and slowest tracks. It has a lonely, bluesy feel created by sparse instrumentation, at least until it builds up into its powerful crescendo. “A broken angel sings / From a guitar” – yeah, that’s pretty much exactly how it feels.

Scarlet Begonias

One of my personal faves, “Scarlet Begonias,” is another flowery song from a band seemingly obsessed with flowers. It just has a great funky groove that may actually have been influenced by the popularity of funk music at the time.

The music was written by Garcia, and the flowery lyrics by Hunter. It was recorded for the 1974 album From the Mars Hotel and later became a staple of the band’s concerts. This is one song that could really get the hippies up and dancing!

Drums/Space

Unlike the other “songs” on this list, Drums/Space is more of an improvisational masterpiece. In live concerts, it became something of a tradition for the band to take a break and let the drummers have some. Bill Kreutzmann and Mickey Hart played off each other, and it was a different experience every time.

Through the use of drums and percussion, electronic instruments, and samples, they managed to create a unique and invigorating soundscape that reached deep into the human soul and pulled out groove.

Shakedown Street

When Garcia and Hunter get together, they seem to continually make magic. With “Shakedown Street,” they did it again. This was the title track to the 1978 album of the same name and features a distinct funky-disco late 70s sound very different from the band’s older material. It’s funky and entirely danceable, and a lot of fun even though it’s a bit of a dark song.

Apparently, “Shakedown Street” used to be the heart of town. Whatever it was written for, this name caught on comically and was used for years by the Deadheads. Whenever a Grateful Dead concert was in town, Deadheads would set up an impromptu market selling everything from Dead-related merch to (possibly magic) baked goods. They started calling this area Shakedown Street in a comic nod to the song.

Althea

This came out on the weird and wonderful 1980 album Go to Heaven. Check out the BeeGees inspired cheeseball album cover!

This track has some of the coolest, funkiest sounds the band ever put out. Written by Garcia and Hunter, the overall feel is a mystical, swampy blues slow burner that later became a concert favorite. The keyboards here really bring a depth and new dimension not heard in a lot of other Dead tracks. It was also a track on an album that sold fairly well and gained the band a much wider following.

Touch of Grey

Touch of Grey” came years later than all the other songs on this list and was accompanied by a touch of grey in the band members’ hair and beards. This single from the 1987 album In the Dark actually made it into the Top 40 and is one of the only songs the Grateful Dead made an official video for.

It has a bit of an 80s synth sound and is definitely poppy, but it’s still the Grateful Dead. And that “I will get by / I will survive” chorus is so hooky; there’s no way you can forget it!

Want to show how much of a Deadhead you really are?

Then get yourself some of the ICUP Grateful Dead Beer GlassesThe Grateful Dead Collectible Large TIn Tote, a Grateful-Dead-Hat 100% Cotton Exquisite Embroidery Baseball Hat, or some Grateful Dead 5 Pack pair Tie Dye ankle Socks for men, all available online in 2022.

Or, to find out even more about this fascinating band, check out A Long Strange Trip: The Inside History of the Grateful DeadSearching for the Sound: My Life with the Grateful DeadThis Is All a Dream We Dreamed: An Oral History of the Grateful DeadDeal: My Three Decades of Drumming, Dreams, and Drugs with the Grateful Dead, or the excellent Home Before Daylight: My Life on the Road with the Grateful Dead.

The Very Best Grateful Dead Songs of All Time

So which is the best Dead song ever? Sorry, you’re going to have to decide that for yourself. Their catalog is just too huge, their songs too improvised and jammed out on to really nail any one song down. Instead, give this band a thorough listen, to both their studio and live tracks, and feel for yourself.

Buy yourself a tie-dyed Dead shirt, watch the Grateful Dead movie, and just enjoy this legendary band that taught us all that “If you get confused, just listen to the music play”!

Happy listening! 

5/5 - (34 votes)
Share:

Leave a Comment

Your email address will not be published. Required fields are marked *

About Warren Barrett

Warren has spent nearly half a century (now that's a long time!) as an ink-stained wretch writing for music magazines and websites and has no plans on giving up soon.

He is curious about all types of music and instruments apart from any genre with 'Urban' in the title. He's also not so keen on Plastic Potted Plants, Reality TV, and any movies with Kevin Costner in them.

He lives in Delaware with his wife Wendy and lots of great memories...

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top