Stand Up and Learn with Kevin Flynn – Westport Country Playhouse

Back by popular demand! Stand Up & Learn™ is an educational program for kids aged 12–16 (email if you’re on the cusp!) that is comprised of a series of lessons using video and interactive worksheets that engage students in creative writing, communication, and critical thinking as well as team and confidence building. Stand Up & Learn is the first stand-up comedy program developed for school-aged children, with an emphasis on writing comedic stories and bits. The program is currently being implemented with Nantucket students, The Gateway School in New York City, the Deveraux Glenholme School in Washington, Connecticut, and at the Cape Cod Conservatory.

Program Details:

The program runs from 3:30pm – 5:30pm Monday through Thursday from August 3 to August 6, 2026.
The performance will take place in the Barn on Thursday, August 6 at 5pm.
The class size will be a maximum of 12 students ages 12 to 16 (email if you’re on the cusp!) Minimum 5 to run.

More about Stand Up and Learn:

In 2007, professional stand-up comedian Kevin Flynn was devastated to learn that a rash of teen suicides had shaken the Nantucket community. Kevin knew there was healing power in laughter, so he set his heart on applying it to the tragedy-stricken island.

Kevin envisioned creating classes for kids using stand up comedy techniques to teach confidence and self esteem. As with any large project, he recognized such an endeavor would require funding. So, Kevin gathered a group of his nationally-recognized stand-up comic friends and asked if they would be willing to donate their time and talent at a Festival dedicated to support the kids’ comedy program. The comics generously obliged.

The following summer, the first Nantucket Comedy Festival brought laughter to a community that was in need of its restorative impact, while laying the groundwork for the revolutionary Stand Up & Learn platform.

More about Kevin Flynn:

Kevin Flynn is an award winning actor, writer, producer, host, and comedian.

Starting out as a professional soccer player, Kevin made the transition to standup comedian by winning the prestigious Boston Comedy Riot. Since that time, Kevin has gone on to make numerous television and film appearances as a comedian and actor.

Kevin can be seen as The Wedding Coordinator in The Heartbreak Kid with Ben Stiller; in Me, Myself and Irene with Jim Carrey; in Osmosis Jones with Bill Murray; and as Charlotte’s Boyfriend in HBO’s Sex and the City. His character, Bram Walker, was voted one of the most popular boyfriends in the series. Kevin recently completed a role in the movie The Worlds Greatest Beer Run with Russell Crowe and Zac Efron.

While constantly acting and performing standup around the country, Kevin also works as a host and entertainer in the sports world. Flynn has covered World Cup Soccer for Fox Sports, ESPN, and ABC. Flynn’s show, SportsFigures on ESPN, received the POLK Award for excellence in children’s programming. He also created a weekly sports podcast for the ESPN Network called Over the Ball. The show combines the worlds of soccer, comedy, and entertainment. The show has been named MLS Talk Show of the Year.

In 1996, Kevin was the host of The Discovery Channel’s Go For It, an extreme outdoor adventure show where he swam with sharks, jumped out of airplanes, and scaled dangerous peaks. The show led Kevin to create his first one-man show, The Go For It Guy, which won the Best of Fest at the Boston Comedy Festival and HBO’s U.S. Comedy Arts Festival in Aspen.

Kevin is currently touring nationally with his latest one-man show, Fear of Heights—A Very Funny Phobia.

Along with continually performing his stand-up, Kevin is also the Founder and Executive Director of the Nantucket Comedy Festival. Each summer, the festival brings top comedic talent to Nantucket Island as the major fundraiser for Stand Up & Learn™, an island-based, year-round comedy education program serving Nantucket’s children. He is in the process of launching the Stand Up & Learn program nationally.

What does the program cost?

The fee for the program is $295 in full. This fee covers four (4) two-hour classes, materials, and complimentary tickets to the performance. We also have scholarships available for those who qualify.

What is the time commitment for students?

Students are expected to attend all meetings from 3:30pm-5:30pm Monday through Thursday from August 3-6:

Monday, August 3 from 3:30pm – 5:30pm
Tuesday, August 4 from 3:30pm – 5:30pm
Wednesday, August 5 from 3:30pm – 5:30pm
Thursday, August 6 from 3:30pm – 5:30pm

Will the performance be open to the public?

The final performance in the Barn will not be open to the general public, but complimentary tickets will be available for reservation to family and friends of students. There will be no charge for tickets to see the final performance.

How do I register for Stand Up and Learn?

Register for Stand Up and Learn by filling out the form below and submitting payment here. Once both payment and the form are received, your spot is secure! Reach out to mmeath@westportplayhouse.org with any questions.

Stand Up and Learn Application (1)

Initial application for Stand Up and Learn educational program for students ages 8 - 16.

Student Name(Required)

First Last

Student Birthday(Required)

Student School

If you are willing, please share what school your child attends (this helps us improve our future offerings and we do not share this information)

Parent/Guardian Name(Required)

First Last

Primary Contact Email(Required)

This email address should be the primary contact for daily communications regarding the program details.

Primary Contact Phone(Required)

This should be the contact number for the primary transportation person to and from the program.

Address(Required)

Street Address Address Line 2 City State / Province / Region ZIP / Postal Code Country

Why would you like to take Stand Up and Learn?(Required)

Please have the student write a short response (2 sentences) describing why they would like to be a part of the program.

Is there anything else you would like us to know about your student?

This is free space to add comments, questions, accommodation requests, concerns, or anything else you would like to communicate alongside this application.

Terms, Conditions and Releases:(Required)

By checking this box, I agree to the Terms, Conditions and Releases below:

The undersigned agrees as follows:
1. Risk and Liability: I understand that during my child’s participation in workshop, although steps have been taken to provide proper organization, supervision, instruction and equipment, it is impossible to guarantee absolute safety. I also understand that I share the responsibility for the safety of my child in workshop, and I assume that responsibility. I shall instruct my child to exercise all necessary caution and to obey the safety instructions of the staff involved.
2. Tuition: Tuition and this form are due in full prior to the first day of the workshop. If a parent/guardian notified the Playhouse that a child is not able to attend any portion of the workshop for which the child is enrolled, any tuition payment(s) previously paid will not be refunded.
3. Release of Liability: I hereby release the Playhouse, its faculty and its employees from all claims of liability, personal injury, loss of personal property and harm while my child(ren) or I dance, sing, act, perform or are on the premises. I acknowledge that I have read and understand all of the information provide to me and agree to all terms and conditions included in this form.
4. Photo Release: I give my permission to use my child’s photographic likeness in all forms of media for advertising, trade, and any other lawful purpose, including photographs for use on the Playhouse’s website, brochures, and advertisements for the Playhouse educational programs. Names will not be used.
5. Behavior Policy: The Playhouse has a zero-tolerance policy for any behavior that could be interpreted as bullying, physical violence, discrimination, or disruptive behavior. I understand that the Playhouse reserves the right to send my child home immediately, should such behavior occur, and remove my child from the workshop, should it be deemed necessary.

By checking the box above, I acknowledge that I have had sufficient opportunity to read the above provisions, and I understand and agree to its specific terms and conditions. In addition, I have read and knowingly agreed to all the release terms included in this document.