The Ultimate Guide to the Best Songs About Toronto

In the Fall 2023 issue of Spacing (coming soon to a store or mailbox near you), we shine a spotlight on five “Toronto Troubadours” — musicians “dedicated to not just writing songs about the city, but 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

One of the five Toronto Troubadours we profiled in the magazine, Kardi could have had a half dozen tracks on this list. But this one stands above the rest.

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

Another entry in our top-five list of Toronto Troubadours, Ohbijou’s Casey Mecija’s songwriting shines in this eloquent ode to loss and longing.

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 got the nod as one of our five Toronto Troubadours for many reasons, including amazing songs like this one. Can you see your house from here?

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

Of course Drake is on this list; he’s on the list of five Toronto Troubadours that we published in the print edition, too. Like many other artists mentioned here, he’s written many times about his hometown. This track and “Weston Road Flows” are arguably the best examples.

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

East end represent! The Lowest of the Low made our list of Toronto Troubadours thanks to their unfailing dedication to writing about their home, with a special focus on places and people on the “other side” of the Don.

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