A lot has changed since we founded Funniest Five in 2013. So in honor of Funniest Five V, we decided to check in with all our previous winners with a questionnaire. Their answers are below, edited for space and clarity.

2016

(Christine Dong)
(Christine Dong)

Where are you now?
Gresham.
What's your current comedy job?
I have a very silly podcast called Chumba and Wumba with Alex Rios, I host a monthly show called Savages at Cider Riot, and I co-host two other shows with friends: You're Welcome on Wednesdays at Mississippi Pizza and Dork Horses randomly at Fixin' To.
What's your biggest accomplishment since placing in Funniest Five?
The birth of my son Palagi Aikae.
What's your biggest regret?
I had my podcast producer rearrange the studio that I record in every Monday, and he did a horrible job. Now it is absolutely shitty in there, and he won't change it back because he has an attitude problem. And since I have nowhere else to record, I have that discomfort to look forward to on a weekly basis.
2. Caitlin Weierhauser

(Christine Dong)
(Christine Dong)

Where are you now?
Portland.
What's your current comedy job?
Lez Stand Up, hosting the I, Anonymous live show at Curious Comedy Theater, teaching Comedy Academy at Helium, running my Harry Potter fan theory podcast, Room of Requirement 237, also co-hosting XRAY in the Morning every Friday with Jason Traeger.
What's your biggest accomplishment since placing in Funniest Five?
I won Portland's Funniest Person Competition at Helium Comedy Club, and took first in the WW readers poll for Best Comedian and appeared in [Portland-made web series] The Benefits of Gusbandry.
What's your biggest regret?
Interviewing for WW the day after Trump got elected.

(Emily Joan Greene)
(Emily Joan Greene)

Where are you now?
Portland.
What's your current comedy job?
I co-host a weekly standup show called Standing Upright.
What is your proudest accomplishment since placing in Funniest 5?
Getting passed at Helium. Being able to work at that club is hands down one of the coolest things I get to do.
What's your biggest regret?
Two months ago, after a good set, I hit up a Redbox on my way home. The residual overconfidence in my system from the aforementioned show resulted in me renting three Blu-rays! In my heart of hearts, I new damn well that I was only going to watch half of one before falling asleep. That night, I flew too close to the sun, and I paid the price. After three days of procrastination, I returned the Blu-rays, resulting in late fees twice the amount I was paid for the show.
4. Don Frost

(Christine Dong)
(Christine Dong)

Where are you now?
Portland.
What's your current comedy job?
Random shows and open mics, mostly taking time to put the pen to the paper.
What's your biggest accomplishment since placing in Funniest Five?
I learned how to wake up before noon.
What's your biggest regret?
Not sleeping past noon anymore.

(Christine Dong)
(Christine Dong)

Where are you now?
Portland.
What's your current comedy job?
I'm regularly working at Helium Comedy Club and Harvey's. My biggest project that I am working on is co-producing a comedy festival called the Undertow Comedy Festival. It's the only comedy festival on the Oregon Coast.
What's your biggest accomplishment since placing in Funniest Five?
Becoming a regular at Helium Comedy Club, getting funding to do this festival, and getting bumped up to do an hour on road gigs in the middle of nowhere.
What's your biggest regret?
If I give myself time to think about regrets and live in the past, I'm not moving forward.

2015

(Ryan LaBriere/WW)
(Ryan LaBriere/WW)

Where are you now?
Portland.
What's your current comedy job?
I do the occasional clubs. I do more fundraising and corporate work now.
What's your biggest accomplishment since placing in Funniest Five?
I was offered to be part of a book about women in comedy called The Girl in the Show by Anna Fields. It is a look at women from Lucille Ball and Gilda Radner to today's funny feminist.
What's your biggest regret?
Life is too short for regrets. I take it one laugh at a time.

(Ryanl LaBriere/WW)
(Ryanl LaBriere/WW)

Where are you now?
Ketchikan, Alaska. [Editor's note: That's not true, and we cannot verify anything else that follows.]
What's your current comedy job?
Currently working at the Black Salmon Tavern as a line cook/bus boy. Tourist season just ended, so business has gotten a lot slower.
What's your biggest accomplishment since placing in Funniest Five?
Leaving comedy for good.
What's your biggest regret?
That I didn't get work on a fishing boat. Some guys can rake in $8,000 a month. I mean, I don't mind my current job: Hours are steady, and I'm able to save up a little here and there. Just got a 32-inch TV for my shed and an extra heater for the pipes (they burst last month, turned the bed to ice, no fun!). In a few years, I'll have enough saved where I can head down to Bellingham and look for a wife. But with a fishing gig, it would be matter of months, not years! Oh well.

(Ryan LaBriere/WW)
(Ryan LaBriere/WW)

Where are you now?
Portland.
What's your current comedy job?
Working on an art, standup comedy, musical, multimedia project called Traeger Method.
What's your biggest accomplishment since placing in Funniest Five?
That I'm still having a great time doing comedy.
What's your biggest regret?
No regrets.

Alex Falcone hosts Earthquake Hurricane (Ryan LaBriere/WW)
Alex Falcone hosts Earthquake Hurricane (Ryan LaBriere/WW)

Where are you now?
Portland.
What's your current comedy job?
I've been lucky enough to open for some great comics as part of their theater shows: Matt Braunger, Demetri Martin and Sebastian Maniscalco. My weekly show Earthquake Hurricane is celebrating our third year, and I published my first novel, a young adult romance about a girl who falls in love with a mummy. Publishers Weekly called it "unfortunate."
What's your biggest accomplishment since placing in Funniest Five?
I just listed my three proudest accomplishments for question 3. Too late to change it.
What's your biggest regret?
On May 9, 2016, I ate an entire tube of cookie dough for breakfast.

(Ryan LaBriere)
(Ryan LaBriere)

Where are you now?
Sherman Oaks, Calif.
What's your current comedy job?
I've been auditioning a lot. I was in a Big Freedia video ("Make It Jingle"), and I've been going on the road opening for Ron Funches.
What's your biggest accomplishment since placing in Funniest Five?
Moving down to LA. I had been in Portland for all of my life. In 33 years, this is the longest I have ever been away, and leaving was scary.
What's your biggest regret?
I'm not a very impulsive person so most of my regrets are petty. Like, I should have had more than a quinoa bowl for lunch, or why did I think Batman v Superman would be better a second time?

2014

Where are you now?
Los Angeles.
What's your current comedy job?
I've been going on the road a lot since moving. Compared to Portland, the sets down here are few and far between. I need to go on the road so I can stay sharp. I've been on a writing team for a pilot, which was one of the best experiences of my life. I'm also lucky enough to be a regular co-host on a podcast called All Fantasy Everything. Ian Karmel started it and we do it every week.
What's your biggest accomplishment since placing in Funniest Five?
Just moving. I was terrified to leave Portland. I'm still scared every single day. Every day that I stay on it down here I'm proud of myself.
What's your biggest regret?
I don't have any regrets. I have the best friends in the world, and whatever I did to get me to this point, I'm thrilled about.

Where are you now?
Los Angeles.
What's your current comedy job?
In addition to performing, I'm currently a writer for The Jim Jefferies Show on Comedy Central.
What's your biggest accomplishment since placing in Funniest Five?
Getting the fuck out of Portland.
What's your biggest regret?
About three months ago, my co-worker Lucas and his wife, Aubrey, welcomed their firstborn son into the world. They named their child Arlo because, as you might have guessed, they met at a record shop and are the whitest couple imaginable. About a week after his son's arrival, I told Lucas that "the name 'Arlo' makes it sound like your son is gonna grow up to be one of those gross dudes who plays acoustic guitar at house parties." Lucas and I haven't spoken since. And though I believe what I said to be true, I do sort of regret having insulted his freshly birthed baby boy.

Steven Wilber
Steven Wilber declined to respond to WW’s request for comment.

Christian Ricketts

Where are you now?
93 miles south of Los Angeles.
What is your current comedy job?
I have been taking time out in order to focus on my transition from standup comedian to real artist—current projects consist of writing a fictional memoir and managing the largest rare 80's pop playlist on Spotify, 'Missed Hits of the 80s'. I feel great.
What is your proudest accomplishment since placing in Funniest 5?
Discovering my voice.
What's your biggest regret?
Voting for Trump.

Where are you now?
Brooklyn.
What's your current comedy job?
I've starting writing for online publications like Hard Drive magazine and also for larger future projects for myself. I've also started a podcast with my buddy Dan Weber called What's More Metal?
What's your biggest accomplishment since placing in Funniest Five?
Getting to open for Kurt Braunohler on his Comedy Central special Trust Me.
What's your biggest regret?
Staying Facebook friends with Martin Cizmar.

2013

Where are you now?
Los Angeles.
What's your current comedy job?
Mostly touring, submitting for various TV and late-night shows, writing, swimming in my pool, and running a show at the Hollywood Improv. I also have a podcast now called Who's Your God? We interview comedians about their religious and spiritual beliefs.
What's your biggest accomplishment since placing in Funniest Five?
Leaving Portland and chasing this dream shit. Also I had dinner with Judy Tenuta, and she told me to stop worrying.
What's your biggest regret?
Getting bullied into this questionnaire!

Shane Torres
Shane Torres

Where are you now?
Brooklyn.
What's your current comedy job?
I tour pretty frequently. I am on the road every weekend for the rest of the year except for one.
What's your biggest accomplishment since placing in Funniest Five?
That I am moving forward in my career and that I have worked hard to get here. I have been very lucky too. Hoping to move to the next level. There are many things to be proud of, though.
What's your biggest regret?
There are many so I will just say the last one.

Nathan Brannon
Nathan Brannon

Brannon did not respond for comment but now lives in LA. Last year, he released his second comedy album on Kill Rock Stars, Because, which was recorded at the Alberta Street Pub. He also runs a podcast called Hamster Village about interracial relationships.

(Emily Joan Greene)
(Emily Joan Greene)

Where are you now?
Tucson, Ariz.
What's your current comedy job?
Still performing, still doing standup showcase Critical Comedy. Right now, I'm working as on-air talent on the classic rock station down here. The Unbookables (a documentary I'm in) was just picked up by Comedy Dynamics. I have a pilot still being shopped and a new album coming out and another to be recorded in spring next year.
What's your biggest accomplishment since placing in Funniest Five?
Probably making my pilot, Life Is Ass.
What's your biggest regret?
For whatever reason, I just couldn't cut it anymore in Portland. I couldn't afford to live there, I couldn't deal with the nouveau riche culture. I wish I could have handled it. I wish I could have stayed.

(Simon Max Hill)
(Simon Max Hill)

Where are you now?
Glendale, Calif.
What's your current comedy job?
Freelance writing, doing the odd set in East LA's thriving alt-comedy scene, and making appearances on podcasts, TEDx, etc. The only difference is, I now write pilots and work on pitches in lieu of playing comedy clubs.
What's your biggest accomplishment since placing in Funniest Five?
Tie between appearing on Comedy Central and mounting my solo show.
What's your biggest regret?
Agreeing to host election night 2016 at Mississippi Studios.

GO: WW's Funniest Five showcase, hosted by Adam Pasi, is at the Alberta Rose Theatre, 3000 NE Alberta St. 7 pm Tuesday, Nov. 28. $10.