Top 25 Grateful Dead Songs: The "Greatest Hits"

Another batch 5 songs drawing from the ones even the most casual of Dead listeners know.

Continuing my series identifying my Top 25 Grateful Dead songs with this batch from the band’s most well-known songs. The Dead aren’t really a band that lends itself to greatest hits or compilations, but there are a few that have crossed over. These are the songs that don’t burnish one’s Deadhead cred, but it’s hard to deny their place amongst the band’s best work.

“Touch of Grey”

This was a song I considered putting in my final top 5 list but it ultimately got bumped out. As I’ve previously discussed, I have a fondness for that late 80s Dead sound one can clearly hear on this track, which was the only Top 10 song in the band’s history.

While it’s a song that’s a bit derided (though that may be too strong of a word) because it was so ubiquitous and gave the Dead a mainstream appeal that took the edge of their countercultural credibility, it’s great both in terms of its lyrics (I mean, “I will get by, I will survive” isn’t so bad as a mantra) and the music. Plus, it led to a wonderful music video that you’d have to be an absolute cynic or have a heart made of stone to not enjoy.

The skeletons standing in for the actual band are all perfect—the Boston Celtics jacket on Mickey Hart, Bobby in his polo shirt, smoking Bill Kreutzmann, it’s a stellar piece of late 80s video work for a band that arose seemingly ages before the advent of the music video.

An interesting question is whether the Dead would’ve been better off without “Touch of Grey” being the big hit it was, as the outsized success of the song put a strain on the group that probably hastened its end… But “Touch of Grey” is a song I enjoy and will frequently listen to even if it’s a bit of an outlier in the Dead’s catalogue.

“Casey Jones”

In a very rare instance, we’ve got a Dead song where the album version is (in my estimation at least) markedly better than any live version. The live version’s of “Casey Jones” lose some of the drive one hears on the Workingman’s Dead recording.

I’m not breaking new ground when I say that the Workingman’s Dead/American Beauty stretch was the band’s peak as a studio endeavor.

While I love the slinky guitar parts, electric and providing a counterpoint to the more acoustic bent of the rest of the album, what makes this song a hit is the drumming. Kreutzmann and Hart are both locked in. It’s that rhythm that gives the song its propulsion, which is also a must for any song which has lyrics like “Driving that train, high on cocaine, Casey Jones you better watch your speed.” It’s the Dead track best suited for classic rock radio (and I mean that in the best sense of the term).

“Uncle John's Band”

Another Workingman’s Dead cut, another one that surprisingly I enjoy the studio version to any live version. It’s also has great “bite-sized” lyrics that make for good little takeaways like “When life looks like Easy Street, there is danger at your door” and “Ain't no time to hate, barely time to wait.”

As is the case with “Casey Jones,” the album version has a bit more momentum to it while the live versions are a little slow for my tastes. Even though it’s an acoustic song, it still has some pep and force to it that gets lost when performed live.

It reflects how many different gears the Dead had that they could produce a song like this and then some of the other songs on this list and elsewhere in this series. This lush, acoustic track comes from the same band that can produce epic feats of musical improvisation and launch into a perfect cover of a Chuck Berry tune.

But this beautiful, lilting tune that is a bit of a Jerry Garcia tour-de-force is one of the best things the band recorded and shows that they could just as easily work within the confines of more traditional pop/rock songwriting as they could in the realms of psychedelic improvisation.

“Scarlet > Fire”

The first of two songs that are well-known because of their importance place in the Grateful Dead live sets, and one that’s a bit of a cheat (as its two songs melded together). There are a few examples of this from the Dead’s history, whether the “China Cat Sunflower > I Know You Rider” or “ Help > Slip > Frank” but this combo is my favorite. They’re just two perfect songs to meld together into one long one.

Not surprisingly, the best version of this according to headyversion.com comes from the Dead’s most famous concert, the 5/8/77 show at Cornell University.

This song usually elicits the best singing by Jerry, or the Jerry singing I enjoy the most, whenever it was performed, particularly on “Scarlet Begonias.”

This and the next song on this list are interesting in that they’re not songs that are “great” because of the album versions but rather from what the songs became in the live setting. Yet if one is thinking of the greatest and most prevalent songs in the Dead’s history, the songs that immediately come to mind when you think of the band, “Scarlet > Fire” certainly comes to mind as does the next song on the list.

“Dark Star”

A song that harkens back to the psychedelic roots of the group and that allows for the trademark improvisation for which the band is famous. Though after 1973 it stopped appearing as regularly in Dead setlist, it’s still enough of a presence for there to be great debate and conjecture about what is the best version of the song. One popular choice is the version from Live/Dead

I was tempted to put “St. Stephen” here because it occupies a similar place in the Dead’s oeuvre but ultimately I think “Dark Star” is more iconic and thus secured a spot amongst these other songs.

Let me know what you think—did I make any mistakes? Am I a fool for loving “Touch of Grey”? And hopefully I’ll be getting back to this series very soon (perhaps the Dead and Company show in Atlanta I’ll be going to will inspire me to keep at it!)