All Episodes

May 5, 2025 56 mins

Jamie Kaler on Comedy, Acting, and Life Lessons: From Homeschooled Special to Working with Legends

In this captivating discussion, comedian and actor Jamie Kaler (known for My Boys, How I Met Your Mother, and Forgetting Sarah Marshall) opens up about his journey in stand-up comedy and acting, including his pandemic-born special "Homeschooled." He shares behind-the-scenes stories from performing in intimate venues, collaborating with comedy icons like Gene Wilder and Bob Saget, and the unique dynamics of working on sitcoms. Kaler dives into why comedy is harder than drama and reveals key career lessons every aspiring performer should know.

The conversation also explores dark humor, grief, and modern parenting, blending laughter with deep personal reflections. From the art and business of comedy to the importance of staying present, Kaler and the hosts exchange wisdom, ending with heartfelt advice to their younger selves—emphasizing empathy, inclusion, and resilience.

Jamie's Socials

IG: @jamiekaler https://www.instagram.com/jamiekaler/ 

FB: https://www.facebook.com/OfficialJamieKaler/ 

YT: https://www.youtube.com/user/jamiekaler 

Chapters
00:00 Introduction and Guest Introduction
 
01:28 Jamie Koehler's Comedy Journey
 
03:30 The Process of Creating 'Homeschooled' Special
 
05:49 Experiences in Sitcoms and Live Performances
 
07:00 Working with Legends: Gene Wilder and Bob Saget
 
11:43 The Challenges of Comedy vs. Drama
 
.css-j9qmi7{display:-webkit-box;display:-webkit-flex;display:-ms-flexbox;display:flex;-webkit-flex-direction:row;-ms-flex-direction:row;flex-direction:row;font-weight:700;margin-bottom:1rem;margin-top:2.8rem;width:100%;-webkit-box-pack:start;-ms-flex-pack:start;-webkit-justify-content:start;justify-content:start;padding-left:5rem;}@media only screen and (max-width: 599px){.css-j9qmi7{padding-left:0;-webkit-box-pack:center;-ms-flex-pack:center;-webkit-justify-content:center;justify-content:center;}}.css-j9qmi7 svg{fill:#27292D;}.css-j9qmi7 .eagfbvw0{-webkit-align-items:center;-webkit-box-align:center;-ms-flex-align:center;align-items:center;color:#27292D;}
Mark as Played

Advertise With Us

Popular Podcasts

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.