Toots Hibbert (1942–2020)

Greg Stewart
4 min readSep 13, 2020

I had the great pleasure of seeing Toots and the Maytals live in 2010. This was a band whose first record came out in 1965. I love them — God, I love them — but I wasn’t expecting that they still had much left in them. But then 67 year old Toots Hibbert bounded up on the stage looking….buff! His baritone, by turns raspy and crystalline, had all of its range and lost none of its energy. Toots Hibbert did that night what he’s done his whole life: created joy.

In tribute to Toots, who passed away on Friday, my five favorite Toots and the Maytals songs.

Pomps and Pride

Most very old reggae and ska broadly falls into two categories: groups where the singer perfectly enunciates the words, often in a Motown style, and groups that you can’t tell what the hell the guy is singing. The ones that go full Jamaican patois. Which is to say, the ones singing in their own voices. Toots was firmly in this latter camp. This becomes a hilarious thing when you write some of the most sing-able melodies ever put on record. Am I right when I sing “Is it a stumbling Iceland, calm down”? Certainly not! But who cares how dumb you sound when the next lines are “Today, today, today is a happy day! And tonight, tonight, tonight is a clever night!” Play this song for your children.

Sweet and Dandy

The Maytals played Sweet and Dandy in the 1972 classic Jamaican film The Harder They Come. The soundtrack for The Harder They Come is….is there a stronger word than “seminal”? Unavoidable side note: here is the complete list of Jamaican movies from the 1970s. Rockers — classic; Shottas — classic; Babylon — classic; The Harder They Come — beyond classic; and Smile Orange — obviously, I must see this! Between the music and the movies — Lord, what were they putting in the water in Jamaica back then!? Trick question: it wasn’t water, it was smoke.

Monkey Man

You know what reggae did better than any other genre? Start a song with one beat and melody and after ten or twenty seconds, switch into something that sounds like an entirely different song. It was like they were bursting with too many ideas so they doubled up each record. Monkey Man starts off with a series of declarative, all-hands-on-board beats — insisting on a dance rhythm that’s doesn’t quite arrive, and then the bassline rolls in and it’s like, oh this is going to be a mellow grooving song. Then the voices of the Maytals — Toots, Raliegh and Jerry — burst in at once: “Aiii Aiii Aiiiiiy! Aiii Aiii Aiiiy! Somethingsomethingsomething Monkey Man!” Turns out you can have a mellow groove song and Toots’ hyper-joyous vocals. God, I love these guys!

Pressure Drop

Many people have surely gotten their first exposure to Toots this year in, of all places, a Coors Light commercial. I’m old school enough to hate when music is sold out, but this is a pretty delightful commercial.

https://www.youtube.com/watch?v=Gwdkk0ouZEA

54–46 (That’s My Number)

Simply one of my favorite songs of any genre. Almost all classic reggae songs are about either joy, the fight for justice, or the Bible. No really. Rastafarians are a seriously devout group. Toots was one of the few “baldheads” who were part of the incredible explosion of music coming from Jamaica in the ’60s and ’70s. Not having dreads did not protect Toots from the rampant police hostility toward reggae singers. His songs were hopeful and uplifting, but also portrayed common people and their struggles against oppression. After a show in 1966, Toots was arrested and jailed for one year for marijuana possession. This is horrific enough, but Toots insisted he was framed. The first verse of 54–46 tells the story of the incident, his primary defense being “how stupid do you think I am?”

And there is only one verse before the party begins. Toots has his Maytals count him up: “Give it to me one time!” “Ungh!” “Give it to me two times! ” “Ungh! Ungh!” “Give it to me three times!” (three times?) “Ungh! Ungh! Ungh!” (yep), “Give it to four times!” “Ungh! Ungh! Ungh! Ungh!” Just as you wonder and hope it will never stop, we break into the chorus: “54–46 was my (prison) number; Right now, someone else has that number.” Repeat, and that’s it. Such a simple protest. They jailed me, turned me into a number, and now another man, potentially innocent, has also been turned into a number. But as with all Toots’ music, it was done with joy, joy, joy! After the chorus, Toots breaks into an extended scat. Has anyone else scatted in reggae? If so, please introduce me to their music, because this song is music at its finest.

Those are my favorites, but that’s by no means all of Toots and the Maytals’ great songs. There is their breakthrough hit Funky Kingston, there is Broadway Jungle, Time Tough, and Bam Bam (later reimagined and admittedly improved upon by Sister Nancy); there are their covers of John Denver’s Country Roads and Radiohead’s Let Down. Have I mentioned Do the Reggay, the song that literally invented the word reggae?

Rest in peace, Toots. You were and will always be an inspiration.

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Greg Stewart

I founded Istic Illic (scripted, advocacy) and cofounded ALL FACTS (docs). I'm also a Managing Partner at GreenSky Ventures, a start-up investor out of Toronto