218 Ossington Ave. Toronto M6J2Z9

OPEN 8 DAYS A WEEK

HAPPY HOURS AT OPEN EVERY DAY

“ “We’re making you sick, maming you and killing you, but you better shut the f*ck up because we’re going to make you sick, mame and kill you” is the message all of us have heard shouted and whispered into our brains through various nefarious means for years now.

My Response: As true as this may be, and it is verifiably true - this old man is indeed making us sick, mamimg us and killing us - it’s still just one befuddled, old man behind a green velvet curtain putting on a grand show - flipping the switches, turning the dials, and pulling the levers of his man-made machine, like in the Wizard of OZ. “

— Sam, The Painted Lady —

Nicky Potter with Gordon Lightfoot
Two women standing behind a bar counter, smiling, with beverage takeout containers in front of them. The background features dark wood shelves with various bottles and barware.
Sam with Lady Gaga's Band
People socializing outside a tiki-style bar with neon signs and colorful lighting.
Group of five musicians performing on stage at The Painted Lady, with guitars, a keyboard, and a violin, in a dimly lit venue.
Group of people at a social gathering, some holding drinks, with a musician playing guitar in front of the group in a dimly lit pub or bar.
Neon sign announcing a weekend dance party with the text "Friday Night" and "Saturday Night" in bright colors. Below, four black-and-white photos show people dancing, socializing, and enjoying live music with drums in a dimly lit brick-walled venue.
A dimly lit bar with people sitting at the counter and socializing. Shelves behind the bar are stocked with bottles of alcohol, and there are chandeliers hanging from the ceiling.
Bartop Burlesque.Spinning glow sticks that form a circular pattern around her hips. The bar has colorful lights, a chandelier, and people seated at the counter.
A three-person jazz band performing on stage in a dimly lit venue. The drummer is in the back, and two saxophonists are in the foreground. String lights hang from the ceiling and a brick wall is in the background.
Flyer for Community Piano Jam event on Saturdays from 3 pm to 5 pm at The Painted Lady, 218 Ossington, with a partially visible piano keyboard at the bottom.
Black and white photo of person playing piano, with hands on keys, reflection of sky and trees on the piano's surface.
Four smiling adults, three women and one man, pose closely together in a bar with colorful neon lighting, brick walls, framed pictures, and a chalkboard menu in the background.
A woman with dark hair and bangs playing an acoustic guitar on stage with red curtains behind her.
People dancing and socializing in a nightclub with colorful lighting, alongside a DJ using a laptop and equipment.
'Open Mic Mondays,' hosted by the Painted Lady. Free red beans and rice on Open Mic Mondays at The Painted Lady while quantities last! Full Backline proveded. Disco ball with a bite taken out of it is also on the poster.
Event schedule for OSS Fest on July 26, 2025, at North Stage. Features performances by The Reposadists, The Rider Raiders, Nelson Sobral, Lucille & Friends, Gruvoria, Iliya Vee's Hypothesis, The Rony Boys, U.N. Jefferson, and Dopamine Dream, with a n
A promotional poster for an open mic night featuring a painted lady butterfly and text details including date, host, location, and sign-up time.
A pint glass with a dark beer and foam with the Cowbell Brewing Co. logo, a glass of light-colored beer behind it, and framed photos on a dark wall with purple lighting in the background.
A group of people gathered in a dimly lit room, smiling and celebrating, with some holding drinks. The atmosphere appears festive and joyful.
Bredren Reggae. A man with a beard and a beanie hat is singing into a microphone while playing a blue electric guitar on a dark stage.
Menu for The Painted Lady featuring cocktails, beers, eats, snack attack, and drinks, with a vibrant teal wall, gold-framed pictures, and a mirror in the background.
Street scene outside a café with outdoor seating, people sitting and socializing, and a storefront with bamboo decor and mannequins, one wearing colorful clothing. Large beautiful solid mahogany bar inside. Vodka, whisky, bourbon, beer.
A glass of mojito cocktail with ice, lime, mint leaves, and a black straw on a wooden table outdoors.
People socializing at an outdoor patio with wooden dividers and a canopy. Some are seated at tables, others are standing, with urban brick buildings in the background.
A woman with long brown hair playing a grand piano decorated with colorful lights, singing into a microphone, in an indoor venue with neon lighting.
Framed photo of two men sitting together, one with long blond hair and a sleeveless shirt, the other with curly black hair and sunglasses, against a colorful background.
A musical performance on stage with a female singer Elise LeGrow, a guitarist, and a drummer. The stage has a sign that reads 'The Painted Lady' and red curtains.
Musicians performing live on stage at The Painted Lady venue. The main musician plays an electric guitar and is in front, with a second musician playing a bass guitar behind them. Stage lighting and a sign with the venue's name are visible.
Backlit bar shelf with various bottles of liquor, beer bottles, and draft taps, set against exposed brick wall.
A glass of beer and a cocktail on a dark mahogany bar counter with colorful blurred lights in the background
Crowd dancing in a nightclub with colorful lights, chandeliers, and decorative string lights.
Two young men playing electric guitars on stage with a drummer behind them, in a dimly lit venue decorated with string lights and a disco ball.
A close-up of a drum set with a glittery blue drumhead in a dimly lit bar or club, with blurred figures of musicians and audience in the background, illuminated by warm, colorful lights.
A man playing an acoustic guitar on stage at a venue called The Painted Lady, with red curtains and a sign in the background.
Sidewalk front summer patio view of a live music bar with outdoor seating, including people dining and a chalkboard sign outside that reads 'Back Patio Vacation Vibes Open.'
A woman at a dimly lit bar with red and green lighting, surrounded by bottles of alcohol and bar equipment.
A woman bartending behind a bar with liquor bottles, with dim lighting and warm ambiance at a nightclub or bar.
A woman in lingerie dancing on stage in a dimly lit nightclub with chandeliers and colorful lights. Burlesque. EDM. Rock'n'Roll. Funk. Disco. Dance. House. Hip Hop. Afrobeat. Jazz. Blues. Dating. Live Music.. Piano Bar.
Crowded bar or nightclub with dim lighting, chandeliers, and framed pictures on the wall, with people gathered around tables and a stage area in the background. Burlesque. EDM. Rock'n'Roll. Funk. Disco. Dance. House. Hip Hop. Afrobeat. Jazz. Blues.
A band performing on stage at a venue called The Painted Lady, with four members: a guitarist with tattoos playing an electric guitar, a vocalist with a painted guitar and a bandana, and two bass players in black shirts, one with a beard and short ha
A group of four people performing live music in a dimly lit venue with colorful string lights overhead. One person is playing guitar, another is playing keyboard, and two are singing into microphones.
Two women in glamorous outfits are sitting at a table outside a building, enjoying pizza, while a man leans over the table smiling at them. Burlesque. EDM. Rock'n'Roll. Funk. Disco. Dance. House. Hip Hop. Afrobeat. Jazz. Blues. Dating. Live Music.
Two women sitting outside a tropical-themed juice bar, smiling and holding spoons, with signs advertising organic juice and smoothies behind them.
Three female musicians performing on stage: one with an accordion and microphone, another with a ukulele and microphone, and the third with an electric guitar and microphone. They are in a music venue with a sign behind them reading "The Painted Lady
Backlit bar shelf with bottles of alcohol, beer bottles, and a beer tap system in a dimly lit bar.
A woman with dark hair, red lipstick, and a big smile sitting on a bar counter in a dimly lit bar or nightclub. She is wearing a bikini top, with her legs extended across the bar. The background shows colorful, blurred lights and patrons. Burlesque.
A woman with blonde hair is playing a black grand piano while singing into a microphone. She is wearing a black lace dress and is seated on a upholstered bench. There are large green leaves behind her. Overlaid text promotes a community piano jam eve
A black and white logo for The Painted Lady, a Rock'n'Roll Burlesque Bar in Toronto, featuring a pin-up style woman sitting with plants around her, and decorative roses and banners with text.
Three men standing together with arms around each other inside a performance venue with a sign that reads "The Painted Lady" in the background. The man in the middle wears a black hat and black shirt, the man on the left has glasses hanging from his
A woman in a purple dress dancing on stage at a nightclub with a striped performer and audience watching.
A group of five people sitting inside a vintage-style booth with dark curtains and yellow trim. The woman in the center has curly blonde hair and is wearing a black outfit with a large red flower on her chest. She is wearing black tights and sneakers
Poster for a blues and burlesque event titled "Le Cabaret Bleu" featuring a woman in vintage burlesque costume holding a microphone, with text indicating live performances, prizes, games, and more, scheduled for December 11th at The Painted Lady.
Crowd of people dancing and enjoying themselves at a lively bar and club called The Painted Lady in Toronto on Ossington Avenue, with colorful artwork on the walls and chandeliers hanging from the ceiling.
Gorrdon Lightfoot at The Painted Lady 2017 
Gordon Lightfoot with Nicky (Co-Owner) 2017

SHOWS

Featured
Darryl Hannah & The Goddamsels
Oct 18
Darryl Hannah & The Goddamsels

Toronto’s Darryl Hannah joins prairie alt-country duo The Goddamsels for a special double bill at The Painted Lady. Expect dreamy country-tinged soundscapes, rich harmonies and a night that moves between psychedelic twang, folk, pop and modern alt-country.

Tickets: $15 Advance / $20 at the Door

BUY TICKETS HERE

Read more →
Sing-a-long w/ Svetty Karaoke 10pm-LATE
Oct 18
Sing-a-long w/ Svetty Karaoke 10pm-LATE

🎤 NO REGRETS. JUST KARAOKE. ✨

Big songs, questionable dance moves, unexpected duets and absolutely NO shame. Grab the mic, channel your inner superstar and sing your heart out at The Lady.

Talent optional. Enthusiasm mandatory. 🍸💋

10PM till LATE | FREE EVENT

Read more →
Open Mic Mondays w/Kunle
Oct 19
Open Mic Mondays w/Kunle

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.


Read more →
BIG SHINY BAND
Oct 20
BIG SHINY BAND

Dive into the Big Shiny Tunes era with Big Shiny Band! Everyone's favourite 90s and 00s rock anthems - from your Discman right into your ears. Sing along, jump along, and come rock out with your top 8 Myspace friends.

$10 / PWYW

8pm-10pm

Read more →
The After Show
Oct 20
The After Show

The night doesn’t end when the show wraps — it just shifts gears.

with DJ Kasey Riot

Bartop: Sarah G & Kimora Koi

11 PM till late

Read more →
WINESDAY Happy Hour live sing-a-long piano w/ Heidi Savoie
Oct 21
WINESDAY Happy Hour live sing-a-long piano w/ Heidi Savoie

🎶 6–9PM | 🍾 $5 Glasses of wine

Read more →
Kinetic: an EDM Party
Oct 21
Kinetic: an EDM Party

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

Read more →
Scone Age Thursdays
Oct 22
Scone Age Thursdays

Scone Age Thursday hits The Painted Lady this month with T—raw rock ’n’ roll, experimental energy, and local Toronto heat.

Featuring:Ok Ok, Rat Quartet, The Brghlights

Doors 9:30PM • Music 10PM • $10

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A Painted Lady Friday Night
Oct 23
A Painted Lady Friday Night

Join us at 10PM for bartop burlesque, DJs, dancing, and just the right amount of trouble. 🍸🔥

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Jelly Roll Piano Jam
Oct 24
Jelly Roll Piano Jam

SATURDAY PIANO JAM

Every Saturday

3PM–5PM • No cover

All skill levels welcome.

Saturdays were made for piano music, cold drinks and hiding out at The Painted Lady. Two easygoing hours of songs, singers, surprises and whatever little bit of magic happens to wander through the front window. Our beautiful Yamaha U3 is waiting, so if you’ve got a song in your fingers, come play. Featuring a rotating crew of guest hosts

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A Painted Lady Saturday Night
Oct 24
A Painted Lady Saturday Night

✨ SATURDAY NIGHT AT THE PAINTED LADY ✨

Cold drinks, hot music, bartop magic, and a little late-night mischief. Come get into trouble with us. 🍸💋

10pm | $10

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NSAI Songwriters Afternoon hosted by Dave Woods
Oct 25
NSAI Songwriters Afternoon hosted by Dave Woods

Join us for the Toronto Chapter's NSAI Songwriters Afternoon hosted by Dave Woods on Sunday, October 25th at the Painted Lady! NSAI stands for the Nashville Songwriters Association International - founded in 1967 - and their motto is It All Begins With A Song. The afternoon will open with featured perfomer Avery Simpson sharing 3 songs & her thoughts on songwriting. Then, a dozen local songwriters will share one song each & the story behind it. This is a great event for music fans & for other songwriters to network. Don't miss this very special afternoon dedicated to the art & craft of songwriting!

FREE EVENT!

Doors 2:30pm

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Jukebox Jordo
Oct 25
Jukebox Jordo

EVERY SUNDAY • 7PM–9PM
NO COVER

Warm up for Sunday karaoke with Jukebox Jordo, a dynamic local one-man-band bringing live looping, percussion, and spontaneous energy to The Painted Lady every week.

Read more →
Soul Sunday Party
Oct 25
Soul Sunday Party

SOUL SUNDAY PARTY

10:00pm til close

NO COVER

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Open Mic Mondays w/Kunle
Oct 26
Open Mic Mondays w/Kunle

📋 Sign-up in person at 8PM (no online sign-ups)
🎶 Feature Artist Showcase 8:15–9PM
🎤 Open Mic 9PM–2AM • 2 songs per performer

Every week kicks off with a different feature artist. Want to be one? DM us on Instagram @openmicmonday.


Read more →
The After Show
Oct 27
The After Show

The night doesn’t end when the show wraps — it just shifts gears.

11 PM till late
@paintedladyossington

Read more →
Happy Hour Piano Jam
Oct 28
Happy Hour Piano Jam

HAPPY HOUR PIANO JAM - live music 6pm-9pm happy people, special drink prices and Rory Lavelle bringing his piano-pop for a precarious world. Cheers.

Read more →
Kinetic: an EDM Party
Oct 28
Kinetic: an EDM Party

A community-driven, safe-space dance party featuring local resident and guest DJs, producers from Toronto's diverse electronic music scene, visuals, and bar-top burlesque.

FREE | 9PM til LATE!

Read more →
Fear and Loathing in Las Luxxy
Oct 29
Fear and Loathing in Las Luxxy

Sexy costume, dance party, & opera cabaret. Featuring over 10 different Halloween themed acts by an amazingly talented cast and crew 😍•  🎉🥳DOORS 7:30pm SHOW START: 8pm•

Read more →
Halloween Live Band Dance Party
Oct 30
Halloween Live Band Dance Party

Join a band of ghouls for a night of classic tunes and good company!

Instead of staying home, scared of 👻 on Hallow's Eve, join us and our band of ghouls for a night of classic tunes and good company!

Emma Hewson, Danny Zaidman, MIP and Steve Farrugia will trick or treat you to songs such as: Thriller, Ghostbusters, The Addams Family, Highway to Hell and more!

Dress up if you dare (we will be!) and enjoy a drink with some devilishly good looking musicians!

Doors at 6:30pm, music from 7pm-9pm, $15 at the door or in advance

Buy Tickets HERE

Read more →

SOCIALS

View fullsize ✨ THIS WEEK AT THE LADY ✨ Toronto nights are getting colder. The Lady is not. 🔥🍸 Live music, DJs, karaoke, burlesque, patio hangs, $5 wine, Happy Hour — and a tiny room that knows how to keep things hot. Pick your night. Or pick several. We
View fullsize Dive into the Big Shiny Tunes era with Big Shiny Band! Everyone’s favourite 90s and 00s rock anthems - from your Discman right into your ears. Sing along, jump along, and come rock out with your top 8 Myspace friends. @bigshinybandto 7:30 / $1
View fullsize SATURDAY PIANO JAM Every Saturday 3PM–5PM • No cover All skill levels welcome. Saturdays were made for piano music, cold drinks and hiding out at The Painted Lady. Two easygoing hours of songs, singers, surprises and whatever little b
View fullsize Mr. Beeper is a Toronto-based jazz quintet that performs a blend of electric jazz, bebop, soul, and funk. The band is led by guitarist and Emmy-winning composer Steve D'Angelo and features members Steve Lucas on bass, Matt Woroshyl on saxophone,
View fullsize Happy Hour hits different with a piano. 🎹🍷☀️ $5 glasses of wine. Piano requests and fun with @jesserwhiteley Evening hangs. Grab a seat, throw in your favourite request and let us soundtrack your happy hour at The Lady. Come early. Stay later th
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View fullsize ✨ THIS WEEK AT THE LADY ✨ Another week of tiny-room magic, loud nights, good pours and absolutely no reason to head home early. 🍸🎶 Live music, DJs, karaoke, burlesque, patio hangs, $5 wine and Happy Hour all week long. Pick your night. Or pick sev
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View fullsize Toronto grunge, post-punk + dreamy alt vibes at The Lady 😎🎸 6:30PM | $15 🎸 Live Music •
@the.pressures @sadfrancisco__ ⚡ The Pressures — early-2000s alt energy with a little Strokes, Killers + Radiohead. 🌙 Sad Francis — dreamy,
View fullsize Amapiano all night 💙 The Movement 
@themovement.to @zo.hla @kiejah_dj @siwe_k05 @saintcase.jama.mvmnt 9pm / free rsvp
View fullsize Happy Hour hits different with a piano. 🎹🍷☀️ $5 glasses of wine. Piano requests and fun with @rorylavelle Sunshine. Evening hangs. Grab a seat, throw in your favourite request and let us soundtrack your happy hour at The Lady. Come early. Stay l
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View fullsize ✨ THIS WEEK AT THE LADY ✨ Seven nights. One legendary little room. Live music, DJs, karaoke, burlesque, patio hangs, $5 wine, Happy Hour — and the kind of nights that have a habit of going later than planned. 🍸🎶 Pick your night. Or pick sev
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View fullsize SATURDAY PIANO JAM Every Saturday 3PM–5PM • No cover All skill levels welcome. Saturdays were made for piano music, cold drinks and hiding out at The Painted Lady. Two easygoing hours of songs, singers, surprises and whatever little
View fullsize 🦑 TONIGHT AT THE LADY🦑 Two longtime Toronto bands. Two long-awaited returns. One very good Friday night. @squid_mountain SQUID MOUNTAIN + PEOPLE WALKING BY Friday, September 4 • 6:30PM • $15 After more than six years away from the st
View fullsize Nutmeg & The Firm After a month on the road across Southern Ontario, Nutmeg & The Firm return home to Toronto for a high-energy night of rock ’n’ roll at The Painted Lady. Formed after a chance meeting at a bar in September 2025

sending good vibrations to all our MANY friends Everywhere…

WE ARE A 100% INDEPENDENTLY OWNED VENUE.

—> Known for Our Great Sound & Vibe. Pro Gear. Acoustically-Tuned Room. <—

SHOWCASING LIVE ORIGINAL MUSIC TO TORONTO AUDIENCES FOR MORE THAN 18 YEARS.

ARTISTS WHO HAVE PERFORMED HERE or at OSSFEST: AHI, Aysanabee, Alysha Brilla, Bob Lanois, Carole Pope (Rough Trade), Johnny Goood & The Triple O’s (Lady Gaga’s Backing Band), Chris Thomas King (Grammy Winning Blues/HipHop/Americana Artist from Baton Rouge), Colter Wall, Rocco DeLuca, Irish Mythen, Tom Wilson (Junkhouse), Ariana Gillis, Jeff Heisholt (The Trews, Skydiggers, Current Fantasy), Kevin Hearn & Thinbuckle (Barenaked Ladies), Elise LeGrow, Robert Scott (MIchael Buble), Great Bob Scott (Look People), Richard Underhill (Shuffle Deamons), Tim Hamel, Mike Pellerin, Mary Margaret O’Hara, Big Freedia (New Orleans ‘Bounce’ /HipHop), The Mahones, Big Rude Jake, Michael Louis Johnson & Rambunctious, Lemon Bucket Orkestra, Bredren, Spooky Reuben, Paul James Band, Lily Frost, Derek Downham, Michael Phillip Wojewoda (Barenaked Ladies, Spirit of The West, Rheostatics), Julian Taylor, Dave Wall (Bourbon Tabernacle Choir), Gene Hardy, Astrid Foster, Pierson Ross & Dopamine Dream, Al Webster (Amanda Marshall, Jeff Healey, Ian Gillian), Giampoalo Scatozza (Tom Jones, Paul Young), Maurizio Guarini (Goblin), Mark Lalama, Davide Di Renzo (Tom Chochrane), Rich Moore, Donne Roberts (Juno Winner), Nelson Sobral, Iliya Vee, Gruvoria, The Roncy Boys, Wayne Cass, Vincent Jamal, Richard Taylor Group, Brutus Begins, Jay Aymar, Al SpX, Lester McLean, Marc McLean (George Michael, Andrea Bocelli, Billy Joel), Brainfudge, Cleave Anderson (Blue Rodeo), Nichol Robertson, James Paul (Garage Baby, Alanis Morissette), Ron Sexmith, U.N. Jefferson, Evan Redsky, Marc Ganetakos (Lighthouse, Nelly Furtado, Ashley MacIsaac, Film/TV Composer), Leo Valvassori (Alannah Myles), The Manic Boys and Girls Club, Grey Swans, and have worked with Jake Gold/mgmtrust.ca (Legendary Manager of The Tragically Hip, Broken Social Scene, The Pursuit of Happiness) during OssFest, and Richard Flohil (Legendary Music Publicist)…