Henry Sir
Stand-up comedian · New York, NY

Henry Sir

Who Henry Sir is

Henry Sir is a Canadian stand-up comedian and writer from Edmonton, Alberta, a former All-Canadian basketball player who now lives in New York and performs at clubs including the Comedy Cellar and Gotham Comedy Club while touring North America. He has been featured on Comedy Central, Just for Laughs New Faces, Don't Tell Comedy and CBC's New Wave of Stand Up. He hosts the satirical political podcast The Freedom Hour and the social media series Current Events Chirped By A Canadian.

Henry Sir tour dates 2026–27

40 shows from 10 October 2026 to 10 April 2027 in Penticton, Washington, Charlotte, San Diego and 18 more cities.

28 more dates, to 10 April 2027
  • Friday 8 January 2027, 7:00 PM (Henry Sir Live In Thunder Bay) at Campfire Comedy Club, Thunder Bay, ON · Tickets ↗
  • Saturday 9 January 2027, 7:00 PM (Henry Sir Live In Thunder Bay) at Campfire Comedy Club, Thunder Bay, ON · Tickets ↗
  • Friday 15 January 2027, 7:00 PM (Henry Sir Live In Minneapolis) at Sisyphus Brewing, Minneapolis, MN · Tickets ↗
  • Saturday 16 January 2027, 7:00 PM (Henry Sir Live In Minneapolis) at Sisyphus Brewing, Minneapolis, MN · Tickets ↗
  • Saturday 16 January 2027, 9:00 PM (Henry Sir Live In Minneapolis) at Sisyphus Brewing, Minneapolis, MN · Tickets ↗
  • Tuesday 2 February 2027, 8:00 PM (Henry Sir Live In Calgary) at Laugh Shop Calgary, Calgary, AB · Tickets ↗
  • Wednesday 3 February 2027, 7:00 PM (Henry Sir Live In Calgary) at The Laugh Shop, Calgary, AB · Tickets ↗
  • Thursday 4 February 2027, 7:00 PM (Henry Sir Live In Calgary) at Laugh Shop Calgary, Calgary, AB · Tickets ↗
  • Saturday 6 February 2027, 8:30 PM (Henry Sir Live In Red Deer) at Bo's Bar & Stage, Red Deer, AB · Tickets ↗
  • Saturday 13 February 2027, 7:00 PM (Henry Sir Live In Swiftie) at Lyric Theatre, Swift Current, SK · Tickets ↗
  • Tuesday 16 February 2027, 7:45 PM (Henry Sir Live In Winnipeg) at Rumor's Comedy Club, Winnipeg, MB · Tickets ↗
  • Wednesday 17 February 2027, 7:45 PM (Henry Sir Live In Winnipeg) at Rumor's Comedy Club, Winnipeg, MB · Tickets ↗
  • Thursday 18 February 2027, 7:00 PM (Henry Sir Live In Regina) at The Cure Bar, Regina, SK · Tickets ↗
  • Friday 19 February 2027, 7:00 PM (Henry Sir Live In Saskatoon) at Art Bar, Saskatoon, SK · Tickets ↗
  • Saturday 20 February 2027, 7:00 PM (Henry Sir Live In Saskatoon) at Art Bar, Saskatoon, SK · Tickets ↗
  • Friday 26 February 2027, 7:00 PM (Henry Sir Live In Lethbridge) at Good Times Comedy Club, Lethbridge, AB · Tickets ↗
  • Saturday 27 February 2027, 7:00 PM (Henry Sir Live In Lethbridge) at Good Times Comedy Club, Lethbridge, AB · Tickets ↗
  • Friday 12 March 2027, 7:30 PM (Henry Sir Live In Vancouver) at Rio Theatre, Vancouver, BC · Tickets ↗
  • Saturday 13 March 2027, 7:00 PM (Henry Sir Live In Victoria) at OK, DOPE, Victoria, BC · Tickets ↗
  • Sunday 14 March 2027, 7:00 PM (Henry Sir Live In Victoria) at OK, DOPE, Victoria, BC · Tickets ↗
  • Friday 19 March 2027, 7:00 PM (Henry Sir Live In Edmonton *SPECIAL TAPING* - Early Show) at Myer Horowitz Theatre, Edmonton, AB · Tickets ↗
  • Friday 19 March 2027, 9:30 PM (Henry Sir Live In Edmonton *SPECIAL TAPING* - Late Show) at Myer Horowitz Theatre, Edmonton, AB · Tickets ↗
  • Thursday 25 March 2027, 8:00 PM (Henry Sir Live In Raleigh) at Goodnights Comedy Club, Raleigh, NC · Tickets ↗
  • Friday 26 March 2027, 7:30 PM (Henry Sir Live In Raleigh) at Goodnights Comedy Club, Raleigh, NC · Tickets ↗
  • Friday 26 March 2027, 9:45 PM (Henry Sir Live In Raleigh) at Goodnights Comedy Club, Raleigh, NC · Tickets ↗
  • Saturday 27 March 2027, 7:30 PM (Henry Sir Live In Raleigh) at Goodnights Comedy Club, Raleigh, NC · Tickets ↗
  • Saturday 27 March 2027, 10:00 PM (Henry Sir Live In Raleigh) at Goodnights Comedy Club, Raleigh, NC · Tickets ↗
  • Saturday 10 April 2027, 7:00 PM (Henry Sir Live In Philly) at Claude's Comedy Club & Bar, Philadelphia, PA · Tickets ↗

Lineups belong to the rooms and the comedians, and can change; each listing has the last word. Their nights on the Comedy Calendar →

Follow Henry Sir

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At a glance

Based in
New York, NY
Came up through
Just for Laughs New Faces
Podcasts
The Freedom Hour
On screen
Just for Laughs, The New Wave of Stand Up, Comedy Central and 1 more
Next on stage
10 October 2026 — The Hub On Martin, Penticton, BC

Specials, shows and podcasts

On screen

Podcasts

Where they got their start

Came up the same way

Other comedians in SUCDb who came through Just for Laughs New Faces:

The Launching Pads: the shows the comedians came through →

Comedians like Henry Sir

Each linked to them by something on the record — a stage they both came through, a bill, a show, a style or a home town.

Six Degrees of Komic Bacon: how they connect to anyone →

Every stand-up comedian with a page, A to Z →

Questions and answers

Where is Henry Sir performing next?

Saturday 10 October 2026, 7:00 PM (Henry Sir Live In Penticton) at The Hub On Martin, Penticton, BC, then 39 more dates on D.O.C.'s Comedy Calendar. Each show's own listing has the last word.

Are they on tour in 2026–27?

Yes: 40 shows from 10 October 2026 to 10 April 2027 in Penticton, Washington, Charlotte, San Diego, Hollywood, Chandler and 16 more cities.

What podcast do they host?

The Freedom Hour.

What TV shows and films are they in?

Just for Laughs, The New Wave of Stand Up, Comedy Central and Don't Tell Comedy.

Where did they get their start?

Just for Laughs New Faces (New Face).

Where are they based?

New York, NY, as their record gives it.

Who are some comedians like them?

Chloe Radcliffe (also in Comedy Central), Brittany Schmitt (also in Comedy Central), Colin Jost (also in Just for Laughs), Kevin Brennan (also in Just for Laughs) and Marcello Hernández (also in Just for Laughs).

Are you Henry Sir?

This page can be your website, free. Send your bio in your own words, your links, your clips, who books you, a line said about you and your weekly show, and they go on this page beside the dates D.O.C. already keeps. Fans follow you here and get your news in the D.O.C. letter.

Your short address, for your bio: disciplesofcomedy.com/henry-sir

Make this page yours →Your dates on your own siteYour show on a poster

The full SUCDb record

The full record — the career in order, the specials and credits, and the sources for each — is on SUCDb, with a button to add them to your D.O.C., your twelve.

Their SUCDb record →

Sources

Updated 10 October 2026 · the record checked 29 September 2026