Shows

~ SHOWS ~

 

Mon Tue Wed Thu Fri Sat Sun
1
Happy Hour: Half Price Margaritas 4:00 pm
Happy Hour: Half Price Margaritas
Nov 1 @ 4:00 pm – 6:00 pm
 
Krystal Jessup & Edward Sayers 6:30 pm
Krystal Jessup & Edward Sayers
Nov 1 @ 6:30 pm – 9:00 pm
Indie-folk show featuring local singer/songwriters Krystal Jessup & Edward Sayers Krystal Jessup: Self-professed travel junkie, singer/songwriter Krystal Jessup blends her nomadic storytelling with soulful vocals to create a unique collection...
DJ NV & The Lady Konswallow 10:00 pm
DJ NV & The Lady Konswallow
Nov 1 @ 10:00 pm – Nov 2 @ 2:30 am
 
2
Happy Hour: Trashy Sangria $10 // Bucket of Sol $30 3:00 pm
Paige Warner and Chelsea Preston 6:30 pm
Paige Warner and Chelsea Preston
Nov 2 @ 6:30 pm – 9:00 pm
Paige Warner and Chelsea Preston
“Soulful Ontario songstress” (Billboard), Paige Warner, and her band are heading across Ontario for the Bitter/Sweet album release tour. With a captivating voice and catchy alt-pop ballads, Paige’s music touches...
DJ Amoney & Forca 10:00 pm
DJ Amoney & Forca
Nov 2 @ 10:00 pm – Nov 3 @ 2:30 am
 
4
Happy Hour OSP tall can with a Shot of Jamo $10 5:00 pm
OPEN MIC MONDAYS! 8:00 pm
OPEN MIC MONDAYS!
Nov 4 @ 8:00 pm – Nov 5 @ 1:00 am
OPEN MIC MONDAYS! @ THE PAINTED LADY
Join us every Monday for our Open Mic! Hosted by the one and only Kunle. We supply a full back line, a wonderfully sounding room and a FOH engineer. Each...
5
Happy Hour Beer Cocktail: Imperial Royale $10 5:00 pm
Owen Fullerton// Lauren Carson// Liam Colbert// Jamie O’Halloran 7:30 pm
Owen Fullerton// Lauren Carson// Liam Colbert// Jamie O’Halloran
Nov 5 @ 7:30 pm – 11:00 pm
4 songwriters from Toronto and beyond are coming together at The Painted Lady to play stripped down, solo versions of their songs and showcase new material. Owen Fullerton (Willy Nilly)...
6
Happy Hour: $25 Bottles of House Wine 5:00 pm
Piano w/ Heidi 6:00 pm
Piano w/ Heidi
Nov 6 @ 6:00 pm – 9:00 pm
Heidi Savoie Biography Heidi Savoie is a pianist, vocalist, and composer who bends and blends genres to get a unique form of jazz, classical and pop. She draws inspiration from...
KINETIC 9:00 pm
KINETIC
Nov 6 @ 9:00 pm – Nov 7 @ 2:30 am
The Future Underground present: KINETIC a FREE Weds night weekly. A not-for-profit community dance party feat. local residents & city favourites.
9
Happy Hour: Trashy Sangria $10 // Bucket of Sol $30 3:00 pm
Skrizzly Adams 6:30 pm
Skrizzly Adams
Nov 9 @ 6:30 pm – 9:00 pm
Skrizzly Adams is an international indie with 200 million+ streams andclimbing.  With a style considered”modern-day heartland rock”, Skrizzly notes influences from Bruce Springsteento Kanye West. Skrizzly, a 2022 amazon breakthrough...
PULL UP w/ DJ Adverb + Introspkt + Truth feat. Starlotte Satine 10:00 pm
11
Happy Hour OSP tall can with a Shot of Jamo $10 5:00 pm
OPEN MIC MONDAYS! 8:00 pm
OPEN MIC MONDAYS!
Nov 11 @ 8:00 pm – Nov 12 @ 1:00 am
OPEN MIC MONDAYS! @ THE PAINTED LADY
Join us every Monday for our Open Mic! Hosted by the one and only Kunle. We supply a full back line, a wonderfully sounding room and a FOH engineer. Each...
13
Happy Hour: $25 Bottles of House Wine 5:00 pm
Happy Hour: $25 Bottles of House Wine
Nov 13 @ 5:00 pm – 7:00 pm
 
Piano w/ Heidi 6:00 pm
Piano w/ Heidi
Nov 13 @ 6:00 pm – 9:00 pm
Heidi Savoie Biography Heidi Savoie is a pianist, vocalist, and composer who bends and blends genres to get a unique form of jazz, classical and pop. She draws inspiration from...
KINETIC 9:00 pm
KINETIC
Nov 13 @ 9:00 pm – Nov 14 @ 2:30 am
The Future Underground present: KINETIC a FREE Weds night weekly. A not-for-profit community dance party feat. local residents & city favourites.
16
Happy Hour: Trashy Sangria $10 // Bucket of Sol $30 3:00 pm
Grey Swans // Chris Seldon 6:30 pm
Grey Swans // Chris Seldon
Nov 16 @ 6:30 pm – 9:00 pm
Ah, for the love of bare November days! Come get cozy with us at @paintedladyossington this Saturday, 7-9pm. Joining us at 7pm is the incredible Chris Seldon  @chris_seldon_guitars – maker of fine...
DJ NV // Starlotte Satine 10:00 pm
DJ NV // Starlotte Satine
Nov 16 @ 10:00 pm – Nov 17 @ 2:30 am
 
17
Happy Hour: Trashy Sangria $10 // Bucket of Sol $30 3:00 pm
Trivia hosted by Cody Crain 7:00 pm
Trivia hosted by Cody Crain
Nov 17 @ 7:00 pm – 9:00 pm
♥️🧠 GET YOUR BRAINS READY! 🧠♥️ ✏️📒 IT’S MONTHLY TRIVIA NIGHT AT THE PAINTED LADY ON SUNDAY NOVEMBER 17 AT 7PM! 📒✏️ 🍿🎥 AND IT’S THE MOVIE TRIVIA EDITION! 🎥🍿...
Luck Be A (Painted) Lady Musical Theatre Open Mic 9:00 pm
Luck Be A (Painted) Lady Musical Theatre Open Mic
Nov 17 @ 9:00 pm – Nov 18 @ 12:00 am
Luck Be A (Painted) Lady Musical Theatre Open Mic
🎵 LUCK BE A (PAINTED) LADY 🎭 MUSICAL THEATRE OPEN MIC with Donavon LeNabat @thebiglenabski 9:30PM | FREE Immediately following trivia with Cody Crain Donavon, a legend in the Toronto Open...
18
Happy Hour OSP tall can with a Shot of Jamo $10 5:00 pm
OPEN MIC MONDAYS! 8:00 pm
OPEN MIC MONDAYS!
Nov 18 @ 8:00 pm – Nov 19 @ 1:00 am
OPEN MIC MONDAYS! @ THE PAINTED LADY
Join us every Monday for our Open Mic! Hosted by the one and only Kunle. We supply a full back line, a wonderfully sounding room and a FOH engineer. Each...
19
Happy Hour Beer Cocktail: Imperial Royale $10 5:00 pm
The Kimora Show 8:00 pm
The Kimora Show
Nov 19 @ 8:00 pm – Nov 20 @ 12:00 am
Nov 19th – it’s bad bitch o’clock ⏰️ 8 pm doors & 9 pm showtime 💃 THE KIMORA SHOW is back for it’s last show of 2024! 🌟 Raffles, limbo...
20
Happy Hour: $25 Bottles of House Wine 5:00 pm
Happy Hour: $25 Bottles of House Wine
Nov 20 @ 5:00 pm – 7:00 pm
 
Piano w/ Heidi 6:00 pm
Piano w/ Heidi
Nov 20 @ 6:00 pm – 9:00 pm
Heidi Savoie Biography Heidi Savoie is a pianist, vocalist, and composer who bends and blends genres to get a unique form of jazz, classical and pop. She draws inspiration from...
KINETIC 9:00 pm
KINETIC
Nov 20 @ 9:00 pm – Nov 21 @ 2:30 am
The Future Underground present: KINETIC a FREE Weds night weekly. A not-for-profit community dance party feat. local residents & city favourites.
21
Happy Hour: Buck off all Pints 5:00 pm
Happy Hour: Buck off all Pints
Nov 21 @ 5:00 pm – 7:00 pm
 
ARMAGEDDON Feat. Jodie Jodie Roger // Fire Manic // STELLA // XUKASIA 8:00 pm
ARMAGEDDON Feat. Jodie Jodie Roger // Fire Manic // STELLA // XUKASIA
Nov 21 @ 8:00 pm – Nov 22 @ 12:00 am
ARMAGEDDON is a series of grimy, underground Toronto shows created by rapper/producer XUKASIA. It’s designed to highlight left-field, electronic-based artists in the realms of digital hardcore, alt-hiphop, noise music and...
22
International POP Overthrow 7:00 pm
International POP Overthrow
Nov 22 @ 7:00 pm – Nov 24 @ 5:00 pm
International POP Overthrow
International Pop Overthrow Music Festival all weekend long! ADV Tickets are available in the LINK IN BIO on our social media account https://linktr.ee/paintedladyossington?utm_source=linktree_profile_share Friday https://www.eventbrite.ca/e/1076833521049?aff=oddtdtcreator Sat Afternoon https://www.eventbrite.ca/e/1076866349239?aff=oddtdtcreator Sat Evening...
Happy Hour: Half Price Margaritas 4:00 pm
Happy Hour: Half Price Margaritas
Nov 22 @ 4:00 pm – 6:00 pm
 
DJ Djibo w/ The Lady Konswallow 10:00 pm
DJ Djibo w/ The Lady Konswallow
Nov 22 @ 10:00 pm – Nov 23 @ 2:45 am
 
23
International Pop Overthrow 1:30 pm
International Pop Overthrow
Nov 23 @ 1:30 pm – Nov 24 @ 12:30 am
International Pop Overthrow
SATURDAY AFTERNOON https://www.eventbrite.ca/e/1076866349239?aff=oddtdtcreator SATURDAY NIGHT https://www.eventbrite.ca/e/1076867873799?aff=oddtdtcreator Saturday afternoon, November 23 2:00 Neil Traynor 2:45 The Violet Archers 3:30 Clockwise 4:15 Jaimie Vernon 5:00 Blair Packham Saturday evening, November 23 8:00...
Happy Hour: Trashy Sangria $10 // Bucket of Sol $30 3:00 pm
Pull UP w/ Adverb + Guest w/ Starlotte Satine 10:00 pm
Pull UP w/ Adverb + Guest w/ Starlotte Satine
Nov 23 @ 10:00 pm – Nov 24 @ 2:45 am
 
24
International Pop Overthrow 1:30 pm
International Pop Overthrow
Nov 24 @ 1:30 pm – 5:45 pm
International Pop Overthrow
SUNDAY AFTERNOON https://www.eventbrite.ca/e/1076872377269?aff=oddtdtcreator 2:00 Just Jillian 2:45 Dante Matas 3:30 Montgomery 4:15 Tara Van and The Vixens 5:00 Cool Blue Halo
Happy Hour: Trashy Sangria $10 // Bucket of Sol $30 3:00 pm
SOUL SUNDAY w/ DJ NV and Rubie Magnitude 9:30 pm
SOUL SUNDAY w/ DJ NV and Rubie Magnitude
Nov 24 @ 9:30 pm – Nov 25 @ 2:00 am
 
25
Happy Hour OSP tall can with a Shot of Jamo $10 5:00 pm
OPEN MIC MONDAYS! 8:00 pm
OPEN MIC MONDAYS!
Nov 25 @ 8:00 pm – Nov 26 @ 1:00 am
OPEN MIC MONDAYS! @ THE PAINTED LADY
Join us every Monday for our Open Mic! Hosted by the one and only Kunle. We supply a full back line, a wonderfully sounding room and a FOH engineer. Each...
26
Happy Hour Beer Cocktail: Imperial Royale $10 5:00 pm
FREE RANGE MUSIC SERIES: Monique In Reverie, Fire & The Wolf, Rising Ronin 8:00 pm
FREE RANGE MUSIC SERIES: Monique In Reverie, Fire & The Wolf, Rising Ronin
Nov 26 @ 8:00 pm – Nov 27 @ 12:00 am
FREE RANGE MUSIC SERIES 
Step into the vibrant heart of Toronto’s indie music scene at FREE RANGE and join us for an eclectic showcase of diverse sounds and talents. Doors...
27
Happy Hour: $25 Bottles of House Wine 5:00 pm
Happy Hour: $25 Bottles of House Wine
Nov 27 @ 5:00 pm – 7:00 pm
 
KINETIC 9:00 pm
KINETIC
Nov 27 @ 9:00 pm – Nov 28 @ 2:30 am
The Future Underground present: KINETIC a FREE Weds night weekly. A not-for-profit community dance party feat. local residents & city favourites.
2020 Fall / Winter Hours: Noon – 11pm...
Take away frosty cold beer, booze, popular coolers, organic freshly-squeezed juices, and delicious food to go along with it all! Stop by our new Tiki Hut facade and say “Aloha!”......
The Painted Lady’s NEW YEAR’S EVE PARTY! Tuesday, December 31st 2019 THIS IS 2020! * SEXY-HOT! MUSIC! * * HOT! SEXY! BARTOP BURLESQUE! * * JUNO WINNING DJ + SPECIAL......
Toronto Fringe Festival here at The Painted Lady JULY 3rd to 14th, 2019!...
We’ve shot 20 episodes featuring a new, up+coming musical artist each episode. These artists have performed here as special features during our OPEN MIC MONDAYS. Each of these artists showcases......
  CMW DISCOVERY SERIES 2018: “Our focus with ‘The Discovery Series’ has always been on songs, first and foremost. And second to that would be the spotlight – that is, whether the artist is ready for it… That’s a lot right......
  CMW DISCOVERY SERIES 2018: “Our focus with ‘The Discovery Series’ has always been on songs, first and foremost. And second to that would be the spotlight – that is, whether the artist is ready for it… That’s a lot......
  “This is will be one f’n INTENSE night of OFF-THE-HOOK live music. Seriously.” ~ Music + Sound, The Painted Lady ~   The Painted Lady and CMW are officially......
We’ve been doing a full 32 channel multitrack recording for some time now. We have the ability to record every show, every single night to industry standards. As well, we......
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