About The Book

Please Underestimate Me is an exploration of satirical essays which explore the underdog theme of being underestimated is actually a position of power. This work of nonfiction takes the reader on a journey as epic as the Pacific Crest Trail full of comical stories, bizarre situations, and touching memories of Jay Flewelling life.

You can experience Please Underestimate Me as a traditional paperback or listen to Jay and other voice actors perform the audio book. The paperback and audio version will be available on Oct. 23 rd


Please Underestimate Me is an autobiographical sketch comedy-style theatrical event based on Jay Flewelling’s personal essays. Throughout his life, whether he was surviving a Christian elementary school, traveling internationally, or jogging on a public street, Jay has been underestimated. But is being the underdog actually an advantage? Five actors and an ASL interpreter alternately embody Jay and a host of other characters throughout a series of funny, bizarre, and touching situations both scripted and devised.



Jay is a cornerstone performer at Curious Comedy Theater and a member of the powerhouse improv troupe J Names (SF Sketchfest, Out of Bounds Comedy Festival). Jay is a multi-talented comedian and storyteller who has been featured on PRI’s Live Wire!, Kevin Allison’s RISK!, and Mortified. He has performed with Kevin McDonald (The Kids in the Hall) and Colin Mochrie (Whose Line is it Anyway?), and performed his one-man show Work Shmerk in Portland and at the Sand Diego Fringe Festival. Jay produced the short films The Collector and Birthday Boss, which won “Best in Humor” at Dan Savage’s 2015 and 2016 HUMP! Film Festivals respectively. Learn more at jayflewelling.com.

Jason is a well known Portland writer, actor, and director. He is the writer and director of the monthly sketch show Shirts and Skins at Curious Comedy Theater, and the creator of Wonderland. Jason has appeared onstage with Portland Playhouse and Hand2Mouth, in television commercials and series such as Grimm and Leverage, and he can be seen in the upcoming feature film Lean on Pete. Additionally, he spent six years as writer/announcer for PRI’s Live Wire!, and recently directed Bri Pruett’s one-woman show Stellar.