The Ultimate Guide to the Best Songs About Toronto

In the Fall 2023 issue of Spacing, we shone a spotlight on five “Toronto Troubadours”: Drake; Kardinal Offishall; Lowest of the Low; Ohbijou; and Owen Pallett. These five artists were chosen because of their dedication to writing songs about the city, and to uniting the creative communities that helped put it on the musical map.

Unsurprisingly, songs by these artists also represent some of the most well-known and poignant musical tributes to our city, but they by no means tell the whole story. How do I know? Because I made a list, that’s how. I scoured articles, playlists, search terms, and more, and found more than 400 songs that reference Toronto, by nearly 250 musicians spanning every genre.

So, with apologies to the writers of the many songs I didn’t find, and with thanks to all of the list-makers who came before me, I present the following list of 50 Toronto songs by 50 different artists, in alphabetical order by title. Feast your hometown-loving ears on this (and go all the way to the end for the links to the playlist):

1. #IVIVI — Lilly Singh & Humble the Poet

A fitting tribute to our city’s diversity. (Did you figure out what the title means yet? Think Roman numerals.)

2. 416/905 (T.O. Party Anthem) — Maestro Fresh Wes

Maestro is one of Toronto’s original hip-hop representatives, and he chronicles his influence on this track.

3. Ambulance Blues — Neil Young
4. The Anthem — Kardinal Offishall

Who was the first Toronto-born rapper to be widely recognized for representing his hometown in his lyrics, lifting other local performers to stardom, and popularizing a nickname for the city? Sorry, Drake fans, but the answer is Kardinal Offishall.
Jason Drew Harrow came to prominence in Toronto’s vibrant underground hip-hop scene in the ‘90s. He also began to form deep bonds with his fellow MCs and performers — including his 2000 EP, Husslin’, which featured production by legendary Toronto hip-hop pioneers Saukrates and Solitair. But it was Kardi’s 2001 album Quest for Fire: Firestarter, Vol. 1 that made him a household hame, thanks to the hit single “BaKardi Slang” — which popularized the Toronto nickname “T-Dot” (coined by Toronto rapper K4ce).
Though never as internationally famous as Drake, Kardinal Offishall’s status as a quintessential Toronto ambassador is unassailable. Would the Raptors have won the 2019 NBA Championship without his song “Run” as their soundtrack? Maybe, but it wouldn’t have sounded nearly as good.

5. At the Roncies — Jully Black
6. Beverley Street — Blue Rodeo

Jim Cuddy and company tuck many Toronto references into their songs. This one is a great example.

7. Black Ice — Ohbijou

Friends in Bellwoods — now that’s a relatable concept for Torontonians. But you don’t have to tell that to the members of the band Ohbijou; they put together two compilation albums with that title, featuring a number of tracks recorded at their band house on Bellwoods Avenue.
The core of Ohbijou was made up of sisters Casey and Jennifer Mecija, who turned the project into a full-blown band after they both moved to Toronto for school. But they did a lot more than that; Ohbijou became the centre of a supportive and highly creative indie music community. Casey’s lyrics, meanwhile, contain many subtle nods to her adopted hometown, from the sounds of raccoons in the trees to “Black Ice,” which documents a journey down Bathurst Street.
In the decade since Ohbijou disbanded, Casey obtained a Ph.D., made films, and now researches a concept explored on the Ohbjiou song “Balikbayan”: the relationship between sound, belonging, and the deeply Toronto experience of community diaspora.

8. Bobcaygeon — The Tragically Hip
9. Charlyn, Angel of Kensington — Jason Collett
10. Cherry Beach Express — Pukka Orchestra
11. Civic Kiss — Kurt Swinghammer

It’s possible that no one has written more Toronto-centric songs than Swinghammer. This one is a great example, but there are many more — dig deep.

12. Closing Time — Leonard Cohen

R.I.P. The Matador.

13. CN Tower — Michaele Jordana and the Poles
14. The CN Tower Belongs to the Dead — Owen Pallett

Owen Pallett has risen to great heights as a composer, arranger, and violinist — but as they sing in “The CN Tower Belongs to the Dead,” they can still see their house from here.
It all started in the early 2000s. Pallett was playing in The Hidden Cameras, while also fronting their own group, Les Mouches. Crucially, they were also a core member of Blocks Recording Club — a cooperative record label that became a vital pillar of Torontopia. Part music scene, part civic pride movement, Torontopia lifted all boats (including a little magazine called Spacing), and soon Pallett entered the limelight by virtue of their first two albums as Final Fantasy (released on Blocks), and their work with Arcade Fire.
Pallett writes songs about Toronto — none better than “This Lamb Sells Condos” from 2006’s He Poos Clouds — but more importantly, they write songs for Toronto, and represent the best of what the city’s music scene is about: a communal understanding that we’re all in it together.

15. The Coldest Night of the Year — Bruce Cockburn
16. Concrete Heart — Great Lake Swimmers

Tony Dekker is a master at weaving the personal and the universal in his lyrics. Toronto takes the spotlight in this song, and its spiritual companion, “I Will Never See the Sun.”

17. Confessions From a Parkdale Basement — Cuff the Duke

Sidelines of the City, the third album by Oshawa transplants Cuff the Duke, is peppered with subtle Toronto references, but this song lays it all on the table.

18. Contract Killers — Kiwi Jr.
19. Crabbuckit — k-os
20. Demolition Waltz — FemBots

This song can be found on The City, a Toronto-themed concept album by FemBots that received wide critical acclaim, for good reason.

21. Dope Fiends and Boozehounds — Rheostatics
22. Down by the Henry Moore — Murray McLauchlan
23. DVP — PUP
24. Echo Beach — Martha and the Muffins

Even if they had never written a single lyric about Toronto, Martha and the Muffins would belong on this list for the cover art of their 1980 debut album, Metro Music, which features a map of downtown Toronto.

25. The Embassy (223 Augusta) — Henri Fabergé and the Adorables
26. Fam Jam (Fe Sum Immigrins) — Shad
27. Forests and Sands — Camera Obscura
28. Get Dark — The Zolas
29. Hard Deep Junction Blues — Big Rude Jake

Andrew Jacob Hiebert’s premature passing in June 2022 left a big, rude hole in Toronto’s music scene. He was a fixture for more than two decades, and wrote many great songs about Toronto — this one is likely the best known.

30. Jumped in the Humber — Jerry Leger
31. Know Yourself — Drake

Aubrey Drake Graham’s reputation as today’s best-known Toronto troubadour is well earned, and it begins with his lyrics. Drake references Toronto in many songs, but the city is more than just his lyrical muse. His ambassadorship of the Raptors, his formative stint on the TV show Degrassi, and his backstory as the son of a single mom who grew up in an apartment in Forest Hill all contribute to his credentials as a worthy representative of Toronto.
It’s for this reason that Drake is deservedly credited for popularizing the nickname “The Six” (or “The 6ix”) to describe our city — perhaps most famously in the first verse of his hit song “Know Yourself.” Its meaning, he says, is twofold: it’s an area code reference, he explained on The Tonight Show, “and actually, at one point, it was considered that Toronto was broken up into six areas…so it’s all clicking, man.”

32. Let’s Go — The Beaches

This song chronicles the genesis of The Beaches at Rosedale Heights School of the Arts — which, along with Etobicoke School of the Arts and Wexford Collegiate School for the Arts, has produced many Toronto musicians.

33. Metro’s No. 1 Problem — Truths and Rights
34. Mississauga Goddam — The Hidden Cameras
35. Mitzi’s — Luke Doucet

Another tribute to a late and lamented watering hole and music venue: Mitzi’s Sister in Parkdale.

36. Neon Skyline — Andy Shauf

This song is the title track from Shauf’s concept album about the colourful characters he encounters in a night spent at the Skyline diner in Parkdale. A great listen, front to back.

37. The Old Apartment — Barenaked Ladies
38. On Yonge Street — Gordon Lightfoot
39. One People — L’Etranger

How many Toronto punk bands can lay claim to counting two federal politicians in their membership? L’Etranger included future MPs Andrew Cash Charlie Angus in their lineup, and this song was an early MuchMusic staple.

40. Parkdale — Metric
41. Romantic Traffic — The Spoons

Though the lyrics don’t reference Toronto directly, this song wins its place on the list thanks to its classic video, the entirety of which takes place on the TTC.

42. Spadina Bus — The Shuffle Demons

Speaking of the TTC, how could we not include this song? If Spacing had a theme song, this would likely be it.

43. T-Ode — Abdominal ft. Notes to Self

Yes, that really is former mayor David Miller introducing this song.

44. Tell Your Friends — The Weeknd
45. Trinity Bellwoods — Treble Charger
46. TTC Skidaddler — Stompin’ Tom Connors
47. Under the Carlaw Bridge — The Lowest of the Low

When Shakespeare My Butt…, the debut album by Lowest of the Low, was released in 1991, Toronto was a very different place. Band founders Ron Hawkins, Stephen Stanley, and David Alexander were veterans of the city’s Queen West music scene, mainly by virtue of their membership in Popular Front. But their new band’s music hit different, and soon became something of a soundtrack for a burgeoning scene in a growing city.
Best of all, Hawkins wrote lyrics about the people and places he encountered every day as a Torontonian — and he represented both sides of the river equally well, with references to west end streets and east end haunts peppering the band’s timeless songs. The band, like its hometown, has transformed significantly in the past three decades, but the tracks laid down by Lowest of the Low in those halcyon days on Queen West continue to guide Toronto’s indie rock bands today.

48. West End (Yea Eh) — The Sorority
49. Wezied — Clairmont the Second
50. YYZ — Rush

Hungry for more? You can hear these tracks, and many others, via the Toronto Troubadours playlists I curated on YouTube and Spotify.

Todd Harrison is a co-founder and senior editor of Spacing, as well as a Toronto-based musician, teacher, writer, and dad.

Image by Virginia Dimoglou