I made this Memento missing poster bc I have time to waste!

Jul - 27 2014 | no comments | By


I’m Still Alive and Doing Comedy

Mar - 19 2014 | no comments | By

Don’t worry, just because I’ve neglected this thing doesn’t mean I’m not working my ass off. More show announcements, maybe even some videos coming to you soon!

Monkey House Comedy Roulette Series

Aug - 04 2013 | no comments | By

Get your grandmother and bring her in here. I don’t care if she’s in the bathroom. I have some great news and I need to share it!

I shall be hosting a monthly comedy showcase at the Monkey House.

This guy. The well dressed asshole.

Every month there’s a new theme. August’s theme is That’s Just Wrong. That means great comedians saying terrible (and funny) things. Best part, it’s only $5. Facebook events below:

Aug 17th – That’s Just Wrong

Sep 21st – On the Spot

Oct 19th – Lady Parts

Nov 16th – The Fabulous Show

Dec 21st – Sexy Chat with Chicky

$5, good laughs, Monkey House. Say that 10 times fast and then hop on the bandwagon because this wagon is an orgy wagon, the best kind of wagon.

My New Podcast Has Started!

Jun - 30 2013 | no comments | By


I’ve started a podcast with a friend and local comedian, Will Betts. It’s called 14th State Podcast, and each week (or bi-week) we invite a guest on to discuss Vermont-y things and play Vermont-y games.


Check it out here!

Named 1 of 7 comics to watch at Green Mountain Comedy Festival

Jun - 10 2013 | no comments | By



Few in Vermont push their audience’s buttons — and boundaries — quite like Chicky Winkleman. Winkleman, 24, specializes in making crowds uncomfortable. That’s a talent he perfected hosting “Sexy Chat with Chicky,” an open-mic series at Levity during which he would berate performers after their sets from his perch in an armchair onstage. Winkleman is not a shock comic, exactly. But he is often shocking, which bodes well for his upcoming podcast with fellow comic Will Betts, “The 14th State.”

So, tell me a joke… “It turns out that when you change all the ring-back tones on the phones at your job to ‘Call Me Maybe,’ you get fired from the suicide-prevention hotline.”

Read the rest at 7Days here.


GMCF Shows

May - 21 2013 | no comments | By



Hey all, I’ll be at the Green Mountain Comedy Festival this year. Lots of Improv, some Improv Stand up, and I’m hosting a late-night Raunchy show!


Late Night Raunchy Show (That I’m HOSTING)

Event here.



Opening Night Improv Jamboree
Feel Good Charity Improv Show with Spark Arts
Improv Boston and Friends
The Full Vermonty (Musical Comedy/Improv


On the Spot Standup!

Event Info Here

Sexy Chat with Chicky Open Mic

Apr - 07 2013 | no comments | By

The past few months I hosted an open mic at the now-defunct comedy club in Vermont, Levity. It was called Sexy Chat with Chicky. I dressed fancy, talked to people, and made L-O-Ls. The best part was this video I made as a goodbye to this classy open mic. Watch it through to the end, I promise it’ll be worth your time (well as much as anything on the internet can be worth your time).

I’m an alcohlic enabler in a VT anti-driving PSA!

Dec - 24 2012 | no comments | By

Make sure you don’t blink or you’ll miss me. I’m the other scruffy young white guy. But I’m an enabler who lets his drunk friends get into cars and drive home. Am I going to hell? Yes, because I’m Jewish. Am I going to hell because of this video? No. But the character I portray is definitely going to hell. Because he is a drunk driving enabler. Also, because he’s Jewish (all my characters are Jewish).

I grew a beard to be in a sexist comedy show

Dec - 12 2012 | no comments | By

I was in a comedy show a couple months ago and I grew a beard because it was a ‘beard’ show. Sounds sexist, amiright? Ladies don’t grow beards at nearly the rate men do.

So I made a high-school grade video to show how much I believe in sexist values. It’s funny, at the very very very end.

I am in a local commercial for Westaff! Call my Mom!

Oct - 16 2012 | no comments | By

Seriously. I’m not going to talk to her. Last time I called her we talked for atleast 5 minutes. Ugh.

Anyhow, I am in a local commercial in Vermont. You don’t care. I don’t care either, so that’s good. Glad we got that out of the way.

I do have to say that the commercial is pretty funny, mostly because it was well written.

Also, totally sorry about that comment, Mom.