The definitive Grateful Dead playlist

This song is from the band's 10th studio album by the same name released in 1978. The Dead didn't go full disco on this album or with the song "Shakedown Streak," but there are more than a few hints of the vibe. For better or worse, this is one of the more unique tracks within the Grateful Dead catalog. Not for being innovative or anything, but because it took guts from the legendary jam band to put out something it knew would be criticized. 

When the Grateful Dead released Wake of the Flood in 1973, it offered a new vibe and direction for the band. The group's first record following the death of co-founder and keyboardist Ron "Pigpen" McKernan featured a jazzier tone. "Eyes of the World" is perhaps the album's standout track and offers a jazz feel, but it's a sincere offering that isn't as convoluted as some of the band's earlier stuff. Over the decades, "Eyes of the World" can hold its own among all the great musical moments from the Grateful Dead. 

Going back to the Dead's third studio album, Aoxomoxoa (1969), when the group was still a psychedelic rock outfit. "St. Stephen" earned its place in the band's legacy thanks to 1969's Live/Dead, their first live album. For years, "St. Stephen" was a regular part of the Grateful Dead concert performances, regularly taking on marathon length and including a part known as the "William Tell Bridge."

The Dead released "Dark Star" as a single in 1968 and was a long-time highlight of the band's live performances. Usually, one song that lent itself to a full-on jam session — often highlighting the work of drummer Bill Kreutzmann — was a major part of the band's live experience. It can be argued that "Dark Star" was the Grateful Dead's first true classic tune and helped generate word-of-mouth about how talented the group was, especially when it came to playing live.

Arguably the highlight of Shakedown Street. "Fire on the Mountain" has been a longtime staple of live sets for just about every incarnation of the band. Longtime Grateful Dead collaborator Robert Hunter wrote the lyrics, while drummer Mickey Hart composed the music. The track was originally part of an instrumental that the latter performed while working with the Diga Rhythm Band a few years prior.

It can be argued that bassist Phil Lesh was the most underrated member of the Grateful Dead. Perhaps his shining moment within the confines of the band is this lead track from the group's praised 1970 American Beauty album. Lesh composed the music and sang lead on a song that became a live favorite during the band's touring heyday.

The opener to Go to Heaven (1980). The album and this particular tune ushered the Dead into the 1980s and more commercial and mainstream awareness. It's an up-tempo, 1950s-like rocking number that delivers some solid guitar work from Bob Weir and Jerry Garcia. It's also the listener's introduction to new keyboardist Brent Mydland. His talented presence is felt right off the bat on a tune that reached No. 68 on  Billboard's Singles chart. 

There was never a true studio representation for "Wharf Rat," but it was a budding live favorite before being included on 1971's Grateful Dead live album, a.k.a. Skull and Roses. It's one of the many celebrated "story" songs created between Robert Hunter and Jerry Garcia. The tale of a vagabond, "Wharf Rat" has held a special place in the hearts of Dead fans who took to any means necessary, often primitive, to follow the band around the country, which was worn as a badge of honor.

Speaking of the vagabond lifestyle. "Jack Straw" is similar to "Wharf Rat" in many ways. Bob Weir told Sing Out! that the lyrics for "Jack Straw" were partially inspired by the John Steinbeck novel Of Mice and Men.  The song, which opened several Dead shows through the years, was never originally released in studio form but found a good home on the stellar triple-live album Europe '72.

The baby of guitarist Bob Weir. The Grateful Dead played "One More Saturday Night" live in 1971, one year before it appeared on Weir's solo debut album, Ace. The song can be found on various Dead compilation and live albums, notably the stellar Europe '72 triple live album. It's one of Weir's — and the band's — more up-tempo, rollicking numbers that probably doesn't get the credit it deserves.

As good as this American Beauty classic is in studio form, perhaps the best version of "Sugar Magnolia" from a proper listening experience standpoint can be found on the brilliant Europe '72 live record. It's just a special song meant to be played and heard live. In that form, the song goes beyond the "jam" stereotype of the band. Although, the musicianship, especially from Bob Weir, is top-notch. 

It took more than 20 years, but the Grateful Dead finally earned a top-40 hit with "Touch of Grey." From 1987's In the Dark, the band's first studio album in seven years, "Touch of Grey" became a somewhat surprising mainstream hit, reaching No. 9 on Billboard's Hot 100. Not all die-hard Deadheads were fans of this poppy number that some didn't feel represented the band. Or simply put, the Dead had sold out. 

In 1970, the Grateful Dead recorded and released Workingman's Dead and American Beauty. This was the best the band had to offer in terms of classic Dead tunes and sound. The popular "Casey Jones," inspired by the story of train engineer Casey Jones, is the closing number of Workingman's Dead. The song is famously known for this line: "Driving that train, high on cocaine, Casey Jones, you better watch your speed." It's one of the few Grateful Dead tracks that has been in regular rotation on classic rock radio.

Plenty of fans and professional music critics consider "Friend of the Devil" to be the highlight of American Beauty. One of the great "story" songs from the Dead and a prominent moment for Jerry Garcia, complete with his memorable guitar riff. Over the years, the song has been covered to the hilt. Bob Dylan, Tom Petty, and Lyle Lovett are just a few well-known artists who have delivered their version of this classic.

While the actual meaning of "Bertha" has been debated and analyzed over the decades, one thing Dead should agree upon is that it's among the band's best "jams." Meant to be savored live — it's included on the Grateful Dead live record — "Bertha" is a scintillating, up-tempo number that truly cooks. There's a blues quality to the track that is subtle enough to tell that the genre influenced the band but not self-indulgent to the point of annoying the listener.

At its core, American Beauty is an acoustic record — a great one. "Ripple" is a prime example of the album's greatness. Because some of the Dead's most popular songs are found on the same album, "Ripple" tends to get overshadowed. The song has been lauded for its stellar simplicity, from a collective strong musical performance to Robert Hunter's poignant and somewhat philosophical lyrics, which have ties to other songs in the band's vast catalog.

Another track that has spanned all the variations of the Dead family of performances. The highlight of 1974's From the Mars Hotel. Whether citing Broadway shows or picking up on other themes and avenues pursued on other Dead songs, "Scarlet Begonias" offers an easy listening experience in the studio or live form. In the latter environment, the tune was traditionally paired with the aforementioned "Fire on the Mountain" for a popular concert moment. 

We highlighted the finale of Workingman's Dead. Now, the opener. This is another Dead classic that is also a favorite among mainstream listeners (reaching No. 69 on Billboard's Hot 100) and casual fans of the band. From the stellar acoustic work to those traditionally special Grateful Dead harmonies, "Uncle John's Band" might be the perfect song for the novice music fan looking to begin a relationship with the band. It pretty much encapsulates the overall sound and greatness of the group. 

In the vast realm of the Grateful Dead's music, "Ramble On Rose" could qualify as a deep cut. It was first played live in 1971 and found itself on vinyl with Europe '72. However, it's one of the band's more whimsical songs. While the song was never a consistent part of the Grateful Dead's live performances throughout the decades, it just might be the most underappreciated track in the band's catalog.

"What a long, strange trip it's been." No better line sums up the Grateful Dead than this famous proclamation from the American Beauty's signature musical moment. The band never hid what it was. Its members were there for the taking and had no problem chronicling the journey — good or bad. The story of a drug raid on the band in New Orleans while touring during the early 1970s turned into one of the most recognizable blues-tinged rock songs.