Olivia Flood-Wylie: No Half-Measures

May 5, 2024

Photo Credit

Bruce Smith


Valerie Lopez


Valerie Lopez

2024 Moontower Comedy Festival Series

The 2024 Moontower Comedy Festival is blessing us with 2 weeks of comedy, film, live podcast, and afterparties. Comedy Wham is featuring our favorite conversations from this year's festival. Enjoy!

As Olivia Flood-Wylie and I audi­bly and unabashed­ly enjoyed a bowl of truf­fle pop­corn from the Driskill Hotel lounge dur­ing our inter­view, she shared that she had an Irish pass­port. Being one to draw con­nec­tions among var­i­ous fac­toids, I thought there’s got­ta be a U2 song I can ref­er­ence” to cap­ture Flood-Wylie’s adven­tures in com­e­dy. But nope, I keep com­ing back to Sheryl Crow’s If It Makes You Hap­py”, but not in the rela­tion­ship angst‑y sort of way. Pos­si­bly the most pro­found thing that our guest ever heard was from her dad: Do you think it’s rel­e­vant that the only thing that’s brought you joy through all of col­lege is this com­e­dy thing?”

Cheers to Dad, but also cheers to Mom for putting in guardrails for­bid­ding Flood-Wylie from enter­ing show busi­ness until she was 18 despite liv­ing in Los Ange­les (I sim­ply must stop myself from think­ing of anoth­er Sheryl Crow tune about a famous boule­vard!) and attend­ing high school in Bev­er­ly Hills.

How did we get here, to the Driskill Hotel lounge for Flood-Wylie’s debut book­ing on the 2024 Moon­tow­er Com­e­dy Fes­ti­val? Well, it all began with a mono­logue of a since-can­celled com­ic, a detour to whale brain stud­ies, a mis­er­able col­lege expe­ri­ence (save the col­lege com­e­dy club expe­ri­ences), an escape to study abroad in Maas­tricht, Nether­lands, and a serendip­i­tous 8 week improv class at Boom Chica­go in Ams­ter­dam. That last one after her sis­ter heard Seth Mey­ers talk about Boom Chica­go on a pod­cast — see pod­casts do work to make dreams come true!

Do you think it's relevant that the only thing that's brought you joy through all of college is this comedy thing?
Olivia Flood-Wylie's dad

Flood-Wylie took to improv like Ahab’s obses­sion with find­ing his white whale in Moby Dick, though I think the bet­ter ref­er­ence may be the res­cue of Ish­mael by the fleet boat, Rachel. Flood-Wylie was fight­ing depres­sion, but once she took that improv class, a full on res­cue was in effect: I lit­er­al­ly went all in. I decid­ed no hob­bies for me.” She land­ed a spot on the Boom Chica­go house team, began standup, dab­bled in sketch, and even taught improv dur­ing her time in Amsterdam.

When orig­i­nal­ly asked to do standup in Ams­ter­dam, she had only per­fomed standup twice in Los Ange­les a few years back, but had been pro­lif­i­cal­ly writ­ing for some time. She got hooked and nev­er looked back, declar­ing standup as her one true love.”

Remem­ber that sup­port­ive and insight­ful mom and dad from above? When it was time to leave Ams­ter­dam, the pull of fam­i­ly in Los Ange­les (and free rent in LA does­n’t hurt) was too much to resist. But LA as a standup com­ic is, well, a wind­ing road (enough with the Sheryl Crow ref­er­ences!!), and the com­par­i­son to the standup scene in Ams­ter­dam was almost too much to bear. Did you know that in Ams­ter­dam, audi­ences pay to attend open mics?!? We’ve released enough episodes of this pod­cast to know the open mic scene in LA is either pay­ing to per­form or bring­ing audi­ences with you. She just was­n’t into standup for her first few months back home.

Enter quite pos­si­bly the best tag team of emo­tion­al and pro­fes­sion­al sup­port. First was the ther­a­pist who encour­aged Flood-Wylie to do one thing per week to pur­sue her dreams. One of which was to book a venue to record a spe­cial four months lat­er. This would turn out to be her spe­cial, Half and Half (avail­able on Youtube). It’s stun­ning that some­one strug­gling so might­i­ly would com­mit to a big under­tak­ing, and Flood-Wylie admits, I pro­cras­ti­nate just as much on standup as I did on (col­lege) essays.” You’d nev­er know it since the spe­cial is hilar­i­ous, pol­ished, and wor­thy of more than its cur­rent twen­ty thou­sand views.

I literally went all in. I decided no hobbies for me.
Olivia Flood-Wylie

The spe­cial land­ed in front of the eyes and ears of the sec­ond mem­ber of Flood-Wylie’s sup­port tag team, Bruce Smith of Omnipop Tal­ent. Smith has an impres­sive ros­ter of standup com­ic clients, but his sense of devel­op­ing tal­ent is exact­ly what Flood-Wylie need­ed at that time. She began tour­ing the coun­try per­form­ing standup, allow­ing her to dis­cov­er her love of air­ports and talk­ing with bar­tenders before she takes to the main stage. While tour­ing she real­ized just how much she loved standup because it afford­ed her the oppor­tu­ni­ty to present her best mate­r­i­al to audi­ences. In addi­tion to man­age­ment, Smith has offered her plen­ty of advice along the way (you’ll have to lis­ten to the pod­cast for those gems).

Rejec­tion is part of growth these days, but only because Flood-Wylie is get­ting (and grate­ful for) so many more oppor­tu­ni­ties which is push­ing her for­ward. It’s been a mag­i­cal jour­ney if you real­ize it might nev­er have hap­pened if she had­n’t been sup­port­ed by her mom and dad, had­n’t been nudged by her sis­ter, chal­lenged by her ther­a­pist, and pro­mot­ed by her man­ag­er. To be clear, she’s put in the hard work, the writ­ing, the trekking through air­ports, work­ing the club circuit.

As we con­tin­ued to destroy the truf­fle pop­corn bowl, we talked about a TED Talk speech I’d heard some time back encour­ag­ing the audi­ence that they can do hard things”. Flood-Wylie lights up and announces she has that quote on a stick­er on her lap­top. And final­ly, the U2 ref­er­ence revealed itself. It’s a Beau­ti­ful Day” when you can con­nect with some­one over a bowl of truf­fle pop­corn, a TED Talks quote, and with how much we love standup com­e­dy. Sláinte to find­ing your one true love, Olivia and for let­ting us join you for the ride.

Fol­low Olivia 

Olivia can be seen and heard:

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Olivia Flood-Wylie