Frederick “Toots” Hibbert has been my favorite reggae singer (and indeed one of my favorite soul singers, period) since I first heard him when I was around 15. Because 2020 is relentless, we now only have his recordings (including his latest studio album, released soon before he suddenly fell ill), but my goodness are there gems in his discography.

My own discovery of his music began with reading Robert Christgau’s gushing review of the soundtrack to the film The Harder They Come – I went to Cutler’s Records in New Haven and picked up the tape and while I instantly fell in love with Jimmy Cliff’s music (another list, another time) the two Toots tracks totally blew my mind – with all due respect to Jimmy, Bob Marley, Peter Tosh, and others, it hadn’t occurred to me that a reggae singer could sound like the second coming of Otis Redding. I immediately picked up Toots and the Maytals’ first US release, Funky Kingston and that immediately went into heavy rotation as well.

So without any further ado, here are ten personal favorites spanning his lengthy career, presented in chronological order. If you’re on the fence about exploring, start with #4 below and then you’ll most likely be motivated to keep going.

1 ) “Six And Seven Books of Moses” (1963, single)

This early single demonstrates Toots’ joyous voice (not yet as gravelly as it would become) and fascination with theology, while also serving as a great example of early ‘60s Jamaican dance music.

2 ) “54-46, That’s My Number” (1968, single)

Since my first time hearing this ska classic, I’ve wondered exactly how a prison song (and, mind you, one without deliberately cheeky lyrics a la “Jailhouse Rock”) could be this upbeat and groovy. I still don’t really know, but this historically important chapter in Toots’ history is a force of nature.

3 ) “Sweet and Dandy” (1969, from The Harder They Come [Soundtrack])

This infectious tale of a rural wedding made teenage me long to have a context in which to dance like this (with a bottle of cola wine, though I suppose I kind of just imagined a jug of Pepsi or something). So dance I did – thank goodness this was before the days of easily-captured video.

4 ) “Pressure Drop” (1972, from The Harder They Come [Soundtrack] and subsequently Funky Kingston)

Have so few lyrics ever been deployed so effectively? I mean, if you could utterly slay with (if I counted correctly) fourteen words, why would you add more? This is an incredible example of Toots’ singing (at times subtly nuanced, at times wailing) and his unearthly blend with the harmonies of Jerry Matthias and Raleigh Gordon, who at this point were at about the halfway point of their fruitful extended partnership.

5 ) “Take Me Home Country Roads” (1975, from Funky Kingston)

I’ve got a soft spot for covers that reveal the soul songs hidden within tunes in other genres, and this is one of the superlative examples. That this wasn’t actually conceived as a reggae song about West Jamaica is something I still haven’t fully wrapped my brain around.

6 ) “True Love Is Hard to Find” (1976, from Reggae Got Soul)

I actually first heard this tune via Bonnie Raitt’s cover version (and they subsequently duetted on it on his 2004 Toots-with-famous-guests album True Love). All of these versions are delightful, though I’m partial to this perfect example of

7 ) “Famine” (1979, from Pass the Pipe)

Compared to his contemporaries, Toots’ politics tended to be a lot less overtly anti-establishment – for example, he also has a song called “Get Up, Stand Up” unrelated to the Wailers’ song by that name, and his (while delightful) isn’t even political inn nature. But it would be an overstatement to suggest that he did not tackle issues in his music, and this is a musically irresistible example of that.

8 ) “See It My Way” (1988, from Toots In Memphis)

Toots singing classic Memphis soul songs, with the production work and rhythm section wizardry of Sly and Robbie? Why yes, that does sound like a great idea, and indeed it works. While I often turn first to “I’ve Got Dreams to Remember” (one of the album’s Otis Redding covers), I’m also particularly fond of the closing tune on the album, an Afrobeat-infused original by Robbie Shakespeare himself.

9 ) “Let Down” (2006, from Radiodread by Easy Star All-Stars)

The idea of a collective of musicians doing reggae versions of classic pop and rock albums honestly sounded kind of goofy to me when I first heard about it, and I expected something akin to Dread Zeppelin. But actually, it’s kind of awesome, and bringing in Toots to sing this track on their remake of Radiohead’s Ok Computer was kind of a genius move given the way he puts the icing on the cake (and then some more cake for good measure) on their arrangement of this song.

10 ) “Do the Reggay” (2012, from Unplugged on Strawberry Hill)

Over 40 years after this song helped introduce the titular word to the broader musical vocabulary, Toots still made it sound contemporary in this performance. Throughout this stripped-down, acoustic album it’s clear that he could still deliver great vocal performances, endearingly flanked by two of his daughters playing, in a sense, the role of Maytals with their soulful voices.