20. Truckin’ (American Beauty, 1970)
I’m sighing heavily. I don’t really think this is one of the Grateful Dead’s best songs, but I’m bowing to the pressure I feel to include it. For one thing, the line, “What a long strange trip it’s been” is iconic. For another, it’s one of a handful of Dead songs that broke through to the mainstream, still gets airplay, and where the studio version pretty fairly tracks how it was played live. It was their biggest hit, in fact, for the first two and half decades of their careers (until Touch of Grey in 1986). And it details their arrest in Buffalo, and the title is an obscure reference to a Robert Crumb cartoon.
Covers: I love this version…
19. Shakedown Street (Shakedown Street, 1978)
Yeah, it’s disco. Yeah, the studio version sounds like warmed over AM single. But I like it. And I like the studio version. And when I saw them open set one with it, live, and they did a 20-minute jam, I was in heaven.
Further listening: Cosmic Charlie. It took from 1960s psychedelia standards what Shakedown took from late 1970s dance music.
Covers: Love the Dent May cover. May is a great artist–check out his original stuff, too.
18. Althea (Go To Heaven, 1980)
Part of the band’s disco phase (check out the album cover—ugh!), Althea was actually more reggae than disco—a hypnotic song with beautiful, bluesy lyrics. “I told Althea I was feeling lost, lacking in some direction. Althea told me upon scrutiny that my back might need protection.”
This may be the only song in history to use the word “scrutiny.”
17. Gentlemen, Start Your Engines (So Many Roads 1965-1995 (Box Set), 1988)
This is one of Brent Mydland’s songs. He didn’t have many of them, but I loved every single one. I was a huge Brent fan. This one was particularly special because it was so bluesy and gritty, and so uncharacteristic of the rest of the Dead’s songs—with lyrics like, “It’s three AM in the combat zone, gentlemen, start your engines…You can close this bar, but baby I ain’t going…If you lock up the whiskey, give me gasoline, I got a seven grand redline on the black machine. The dead can do my sleeping, if you know what I mean.” It’s also got a lament, much like in the classic song Wharf Rat: “One of these days I’m gonna pull myself together…Soon as I finish tearing myself apart.” Wharf Rat became the theme for members of Alcoholics Anonymous who attended Dead shows and, at halftime, would hold impromptu AA meetings in the halls. In that song, Jerry Garcia sings, “But I’ll get back on my feet, someday, the good Lord willing…” Lyrically similar, but Brent’s feels more like a gutter-bottom drunk—there’s no real home in his song, or his delivery of it.
And it wasn’t just powerfully honest about the alcoholism that would eventually kill Mydland, it was also as tough and mean as an old Rolling Stones tune: “Got a little girl here in a pinafore, she’s gonna do us all and then beg for more…”
I just noticed I wrote more about this than any other song on this countdown. Wild, huh?
The lyrics were by John Barlow
Further listening: Barlow cowrote the other songs Brent sang lead on, the best of which were Blow Away, Easy to Love You, Just a Little Light, We Can Run, and I Will Take You Home. I suggest all of these as further listening, plus Wharf Rat if you like the “hopeless drunk” theme.
16. Foolish Heart (Built to Last, 1989)
The lead single from the band’s last album. Built to Last gets unfairly maligned, in part because Jerry’s voice was so weak you practically hearing him dying on the tracks, and also because there are some pretty weak songs on it: There was lots of Brent—and his song I Will Take You Home came off as treacle (it was much better live), Bobby’s Victim or the Crime and Picasso Moon were just weird, and there were only three Jerry tunes. But as a pop single, Foolish Heart stands up as one of their better ones. That’s my opinion, and I’m sticking to it.
Further listening: The title track from the same album.
Next: More of the countdown!