The Painted Lady

est 2007

218 Ossington Ave • Toronto Ontario

Open 8 days a week

Fully Stocked Bar

Live Music

A circular logo for The Painted Lady in Toronto, established in 2008, featuring a vintage pin-up style woman sitting among flowers, with text indicating offerings such as burgers, ques, live music, great food, and bar.

☕️🍸 DAILY HAPPY HOUR @ THE LADY 🍸☕️
2PM–6PM • Every. Single. Day. Sip, snack, and stay awhile — with organic coffee, craft cocktails, and high-speed internet day or night. Whether you’re working, vibing, or just unwinding, The Painted Lady’s the perfect spot to plug in or chill out. ✨

EVENTS

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EVENTS *

Featured
Open Mic Mondays w/Kunle
Dec 15
Open Mic Mondays w/Kunle

8pm SIGN UP

Everyone Welcome!

Jukebox Jordo
Dec 16
Jukebox Jordo

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

The After Show
Dec 16
The After Show
WINESDAY Happy Hour with Heidi Savoie
Dec 17
WINESDAY Happy Hour with Heidi Savoie
Kinetic
Dec 17
Kinetic

A not-for-profit community dance party featuring music from our local residents and Toronto's diverse electronic communities, producers and DJs each and every Wednesday.

Pop Up Holiday Market
Dec 19
Pop Up Holiday Market

9am-5pm

Community Piano Jam
Dec 20
Community Piano Jam

3PM-5PM
FREE EVENT

Open Mic Mondays w/Kunle
Dec 22
Open Mic Mondays w/Kunle

8pm SIGN UP

Everyone Welcome!

The After Show
Dec 23
The After Show
Community Piano Jam
Dec 27
Community Piano Jam

3PM-5PM
FREE EVENT

Soul Sunday
Dec 28
Soul Sunday

10:00pm til close NO COVER

Open Mic Mondays w/Kunle
Dec 29
Open Mic Mondays w/Kunle

8pm SIGN UP

Everyone Welcome!

The After Show
Dec 30
The After Show
All That Shimmers - An Early New Year's Eve Burlesque Show
Dec 31
All That Shimmers - An Early New Year's Eve Burlesque Show

7pm

Early Bird Tickers $30

After December 1st $35

Buy Tickets Here

KINETIC 145 - NEW YEARS EVE with JELO
Dec 31
KINETIC 145 - NEW YEARS EVE with JELO

KINETIC 145 - NEW YEARS EVE with JELO

9pm | FREE

SOCIALS

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SOCIALS *

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View fullsize 🎹 3–5 PM — Community Piano Jam ✨ Hosted by Windsor Johnson @windsor_johnson ✨ All skill levels welcome ✨ Gorgeous Yamaha U3 waiting in the window ✨ Good vibes + live energy Come play, sing, or just hang — Let’s turn Saturday
View fullsize ✨🎷 LE CABARET BLEU IV: HOME FOR THE HOLIDAYS 🎷✨ We’re decking the halls and dropping jaws !! join us Dec 11 at The Painted Lady for a sultry holiday soirée filled with live jazz, burlesque, drag, games, and glittering surprises. 🎁 ?
View fullsize Tonight! @oridaganjazz
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View fullsize ✨ THIS WEEK AT THE LADY • December 8–14 ✨ Check back daily — new surprises & updates 👀 🎟️ Advance tickets & full details on our website — link in bio 🍸 Happy Hour • Daily • 3–7PM MONDAY DEC 8 🎤 Op
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View fullsize SUNDAY DEC 7
💎 Afterglow • 7PM | $15 Afterglow is a night of R&B and soul in a purple-litToronto space. I’m A$iia, joined by the incredible Joshel and Mont Kapalon, and we’llbe bringing music, vibes, and energy that you can fee
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View fullsize 🎹✨ SATURDAY PIANO JAM! ✨🎹 Join us TODAY from 3–5 PM for a Community Piano Jam — all are welcome! 🎶🎉 Whether you’re a pro or just testing the waters, come play, vibe, and connect with an incredible crew of local musicians 💫🎼 W
View fullsize 👯‍♀️ The Getdown • 10PM til late @theladykonswallow @djamoney
View fullsize 🎶 Henry & Monique Folk Explosion holiday show • 6:30PM | $10 @henrytaylor_45
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View fullsize ✨ THIS WEEK AT THE LADY • DEC 1–7 ✨ 
Check back daily — new surprises & updates 👀 🎟️ Advance tickets & details on our website — link in bio
🍸 Happy Hour • Daily • 3–7PM MONDAY DEC 1
🎤 Open Mic &bull
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View fullsize Saturday November 29! 🎶 Live Music • 6:30PM — @dandelionhighway @rich_freed

OUT AND ABOUT AT THE PAINTED LADY

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OUT AND ABOUT AT THE PAINTED LADY *

Our Community!

Two women singing into microphones on a dark stage, illuminated by colorful stage lights.
Nicky Potter with Gordon Lightfoot
A woman dressed in a feathered costume and feathered headpiece inside a dimly lit bar or nightclub, with framed artwork on a brick wall behind her and a chandelier hanging from the ceiling.
A promotional poster for an open mic night featuring a painted lady butterfly and text details including date, host, location, and sign-up time.
People dancing and socializing in a nightclub with colorful lighting, alongside a DJ using a laptop and equipment.
Kiefer Sutherland and his band
Sam with Lady Gaga's Band
Flyer for a community piano jam event with a background of a piano keyboard and sheet music. The event is open to all and takes place on Saturdays from 3 pm to 5 pm at The Painted Lady, 218 Ossington.
A detailed illustration of a red rose with green leaves and a bud, with the words 'LOVE' in the top left and 'JOIN THE REVOLUTION' in bold text at the bottom.
A woman in a bar dressed in a burlesque style costume with a large red feathered headdress, fishnet stockings, and pasties, smiling at the camera. The bar is lit with warm orange and yellow lights, with shelves of liquor bottles and a couple of peopl
Promotional poster for Grey Swans, Second Saturdays at The Painted Lady, 7-9 PM, featuring illustrated black swallows on snow-covered branches with a pink circle background and black and white trees.
A performer singing into a microphone while playing an electric guitar on stage. The performer has short hair and is wearing a sleeveless patterned top and jewelry. Behind them, a sign reads "The Painted Lady" in red and orange letters, and colorful
A black and white photo of a music performance in a dimly lit venue. There are two people on stage, one holding a guitar, with bright lights shining behind them. In the foreground, a drum set is visible.
Davide DiRenzo with Mark Lalama and Rick Moore
A person dancing on a stage with a digital backdrop that displays the word 'Kinetic' and various geometric patterns, with a DJ performing in the background.
Alysha Brilla and Lisa
Event poster for Free Range music showcase, featuring a performer on stage with a colorful costume and an audience, with the background sign reading "The Painted Lady."
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 collage of nine black and white photos of a woman singing into a microphone, wearing a patterned dress, with colorful paint strokes and the words "sing along with Shetana Kongsawall" and "karaoke".
Two women singing and playing guitar on stage with warm orange lighting.
A black and white collage featuring five women in various poses, with the words 'BART BURETQUE' vertically aligned along the right and bottom. There is a circular logo at the bottom center reading 'FRI & SAT NIGHT' and 'The Painted Lady'.
Logo with the word 'KINETIC' and a stylized globe or sphere in the background, featuring geometric shapes and abstract lines.
Woman taking a selfie in a mirror, wearing red and black lace lingerie, with red hair and a red feathered headpiece, holding a phone in her right hand, touching her face with her left hand.
PA%2Band%2BBubba.jpg
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.
A woman in a red and black outfit performing a split on a stage with musical instruments in the background, neon pink lights, and a sign that reads 'Tainted Lady'.
A group of people gathered in a dimly lit room, smiling and celebrating, with some holding drinks. The atmosphere appears festive and joyful.
neon signs reading "Friday Night," "Saturday Night," and "Dance Party" with black and white photos of people dancing and playing drums at a party, and a circular logo with "The Painted Lady," "10:30 PM," and event details.
Retro-style poster advertising Soul Sunday music event with vinyl records and a skillet, promoting soulful grooves and sound sets at 218 Ossington Ave.
A woman with dark hair and bangs playing an acoustic guitar on stage with red curtains behind her.
Black and white photo of person playing piano, with hands on keys, reflection of sky and trees on the piano's surface.