218 Ossington Avenue . Toronto . Ontario . M6J 2Z9 . Canada

rock ‘n’ roll

funk ‘n’ soul

burlesque

b a r

•

Open

7 days a week

LIVE MUSIC EVERY NIGHT

—> Known 18 Years+ for Our Great Sound & Vibe. Pro Gear. Acoustically-Tuned Room. <—

Winter Hours in effect

Sunday - Friday 6pm - 2am or later

Saturday 3pm - 2am or later

Fully Stocked

B E A U T I F U L

3 4 f o o t l o n g

SILVER DOLLAR STYLE

A R T I S A N ~ M A D E

SOLID MAHOGANY

B a r

SHOWS

Featured
See You on the Dance Floor&nbsp;
Feb 27
See You on the Dance Floor 

🪩 10PM til Late | $10

Community Piano Jam
Feb 28
Community Piano Jam

3PM-5PM
FREE EVENT

Retro-spects with Superchannel
Feb 28
Retro-spects with Superchannel

6:30pm | $15

TURN IT UP — 10PM DANCE PARTY 🎧✨
Feb 28
TURN IT UP — 10PM DANCE PARTY 🎧✨

10pm til late | $10
SEE YOU ON THE DANCE FLOOR

Sing-a-long w/ Svetty Karaoke
Mar 1
Sing-a-long w/ Svetty Karaoke

10PM till LATE

FREE EVENT

Open Mic Mondays w/Kunle
Mar 2
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.


Ashley Ghostkeeper with Sean Donley
Mar 3
Ashley Ghostkeeper with Sean Donley

7:00pm | $20 TICKETS HERE

The After Show
Mar 3
The After Show

10pm ‘til Late

WINESDAY Happy Hour with Meher Steinberg
Mar 4
WINESDAY Happy Hour with Meher Steinberg

6pm-9pm

$5 Glasses of wine

Kinetic
Mar 4
Kinetic

9pm-2am

A FREE not-for-profit community dance party!

Fletcher Daniel with Hey Buddy, Hey Champ
Mar 5
Fletcher Daniel with Hey Buddy, Hey Champ

7pm | $15 TICKETS HERE

Live Music Karaoke
Mar 5
Live Music Karaoke

10pm / FREE

Community Piano Jam
Mar 7
Community Piano Jam

3PM-5PM
FREE EVENT

TRAUMAQUEEN, with guest Jordan Wav.
Mar 7
TRAUMAQUEEN, with guest Jordan Wav.

Get ready for a high-energy night of modern rock at full throttle 6:30PM | $15

TICKETS HERE

Jukebox Jordo
Mar 8
Jukebox Jordo

7:30 PM • Pay What You Can ($15 suggested)

SOCIALS

View fullsize ✨ HAPPY WINESDAY AT THE LADY ✨ WEDNESDAY &bull; FEB 25 🍷 $5 glasses all evening 🎹 Live magical piano with @mehersteinberg starting at 6PM Settle in, sip something beautiful, and let the midweek melt away. Then we turn it up&hellip; ⚡ KINETIC &m
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View fullsize ✨ THIS WEEK AT THE LADY ✨ February 23 &ndash; March 1 ❄️ Winter Hours in Effect (unless otherwise noted) Sunday&ndash;Friday: 6:00 PM &ndash; 2:00 AM (or later) Saturday: 3:00 PM &ndash; 2:00 AM (or later) 👀 Check back daily for surprises 🎟 Tick
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View fullsize We&rsquo;re OPEN EARLY this Sunday 🇨🇦🏒 The Team Canada Olympic hockey gold medal game kicks off at 8:10AM ET &mdash; and we&rsquo;ll have the doors open, the sound up, and the coffee (and cocktails) flowing. Throw on your red &amp; white, bring
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View fullsize SATURDAY &bull; FEB 21 🎹 Community Piano Jam &mdash; 3:00 PM @matteo.m.caruso
View fullsize FRIDAY &bull; FEB 20 🎧 The Movement &mdash; 9:00 PM @themovement.to &bull; @saintcase &bull; @hiddenlotvs &bull; @barithisbarithat &bull; @saintcase.jama.mvmnt &bull; @jeffersxonn &bull; @starlottesatine FREE BEFORE 11PM
View fullsize TUESDAY &bull; FEB 17 🥳 Happy Mardi Gras We&rsquo;re bringing a little Bourbon Street energy to Ossington 💜💚💛 Beads, beats, and a whole lot of bad decisions (the fun kind). Come celebrate Mardi Gras with us &mdash; big vibes, big moves, and that
View fullsize ✨ THIS WEEK AT THE LADY ✨ February 16&ndash;22 ❄️ Winter Hours in Effect (unless otherwise noted below) Sunday&ndash;Friday: 6:00 PM &ndash; 2:00 AM (or later) Saturday: 3:00 PM &ndash; 2:00 AM (or later) Check back daily for surprises 👀 🎟 Ticket
View fullsize LONG WEEKEND SUNDAY &bull; FEB 15 🎶 Live Music: 7:00 PM Mr. Beeper @dangelo_steve hits the stage with a slick blend of electric jazz, bebop, soul &amp; funk. Led by Emmy-winning guitarist Steve D&rsquo;Angelo and featuring Steve Lucas (bass), Matt
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View fullsize ❤️ Live Music &mdash; 6:30 PM @greyswansmusic &bull; @jax.turcotte
View fullsize 🎹✨ SATURDAY PIANO JAM! ✨🎹 Join us TODAY from 3&ndash;5 PM for a Community Piano Jam &mdash; all are welcome! 🎶🎉 Whether you&rsquo;re a pro or just testing the waters, come play, vibe, and connect with an incredible crew of local musicians 💫🎼 W
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“chEERS!” and a “Big up!” To all our MANY friends Everywhere… Thank you ossington avenue community! Thank you toronto!

WE ARE A 100% INDEPENDENT VENUE THAT HAS DEVOTED OVER 18 YEARS TO SHOWCASING LIVE MUSIC IN TORONTO.

ARTISTS WHO HAVE PERFORMED HERE: AHI, Aysanabee, Bob Lanois, 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, 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, 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), Alarm Alarm, Donne Roberts, 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, Richard Flohil (Legendary Music Publicist)…

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.