Olivia Flood-Wylie: No Half-Measures

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!

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.

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 

• Insta­gram — @oliviafloodwylie
  
• Tik­Tok — @ofw.comedy
• YouTube — Youtube​.com/​O​l​i​v​i​a​F​l​o​o​d​-​Wylie

Olivia can be seen and heard:

• Half and Half — 2023 Com­e­dy Special