Maui Arts & Entertainment

Smartest Man in the World: Comedian Greg Proops on Maui

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Greg Proops. Courtesy photo.

Greg Proops. Courtesy photo.

By Cassandra Hastu

Maui’s largest comedy festival is coming to Lahaina on Halloween weekend.

The three day event will take place at six different locations all within walking distance of each other on Front Street, in the heart of Lahaina.

The festival will include thirty plus comedians who have appeared on Comedy Central, NBC, ABC, HBO, and all the big networks.

On one special night the Old Lahaina Prison will transform into a theater for Hawaiian born comedians to showcase their talent and create laughter for all to enjoy.


Among the list of featured comics is Greg Proops of San Francisco (now living in Hollywood), who is know for his unpredictable appearances on Whose Line is it Anyway?, and hosts his own hit podcast, The Smartest Man in the World.  He can also be seen on the New Season on the CW, and the new season of @midnight on Comedy Central.


We were lucky enough to catch up with Proops and ask him a few questions about Maui and about comedy in general.

Q: Are you looking forward to coming to Maui and have you been to Hawaiʻi before?

A: Yes and Yes. I am looking forward to coming to Hawaiʻi, to Maui. I have not been to Maui I have been to the Big Island, Oʻahu, and Kauaʻi. I am excited about coming to Maui.


Q: What adjustments do you have to do to your stand up routine when travelling to different parts of the world?

A: Well, I think you have to take into account where you are and understand that people’s sensibilities are all different and they might have a different attitude then the Americans. Last night I did a show and English was not the first language so I slowed it down a little bit. I still try to be funny obviously.

Q: What do you most look forward to when travelling to Hawaiʻi?

A: To Hawaiʻi? Well I mean the relaxation it will be nice not to have to bring rain clothes. We are looking forward to the nice weather. We are going to get a car and drive around the island so we can see lots of things.

Q: From your first comedy show to now, how have you changed?

A: Really? You wrote that question on your own didn’t you? Well my first comedy show was when I was 18 and that was quite a while ago. I think in rapport I am the same, I am still a show off and I want people’s approval that is the sickness of being a comic. I have become way more honest and I’m not afraid anymore to challenge the audience or to fail. It takes a while to learn that failure is the key to comedy.

Q: You will have one night off between shows here in Lahaina, and that night is Halloween. Any plans? Who are you dressing up as for Halloween?

A: It is hard for me to dress up because I have to wear glasses. I am too old to go as Buddy Holly. I heard you have something called Night Crawlers, that sounds fun we will probably walk around for that.

Q: Where do you come up with most of your material?

A: Well I travel a lot so I am always reading the paper everywhere I go and watching the news and keeping up with things. I am usually thinking about what’s happening and telling stories about what I’m doing and how I feel about politics. My political view point forms a good deal of it. And I’m a screaming liberal from San Francisco.

Q: If you haven’t already, when do you think you will know you have accomplished all you’ve set out to do?

A: Never. You are never done accomplishing. I always want to be more clever, more charming. That’s the charms of life, it’s not to be perfect, but to try all the time.

Q: What makes a very funny person like you laugh?

A: My wife, she is really funny, she gives me lots of good ideas, and she’s my partner in everything. I love comedy still. I think there are lots of great comedians out there. A lot of people coming to the festival make me laugh.

Q: What is your fondest memory since you have started your career?

A: I got to meet and work with Robin Williams and Joan Rivers. I have done shows in England with Michael Palin and Terry Jones from Monty Python. I just did an improv show with Eric Idle in Seattle. I think the nicest part is I’ve met people like Drew Carey and Ryan Stiles and they’ve been unbelievably kind and generous to me and I think that’s probably the grooviest part.

Q: What can we expect from you in the future?

A: Well I have a book coming out next year called The Smartest Book in The World. I’m going to carry on doing my podcast everywhere. This year I’ve done it in Toronto, San Francisco, New York Paris, Amsterdam, Helsinki and I just did one last night in Antwerp (we did it last week in London). I hope to expand the horizon and go to different places like Mexico and Asia.

***Greg Proops can be seen at the following Maui Comedy Festival events:

  • Thursday, Oct. 30, 2014, 7 to 8:30 p.m. at Longhi’s in Lahaina: The Smartest Man in the World – Live Podcast with Greg Proops.
  • Sunday, Nov. 2, 2014, 5 to 6:30 p.m. at Hard Rock Cafe at The Outlets of Maui: Shut Up, You Might Learn Something – with Greg Proops, Ahmed Bharoocha, Aparna Nancherla, and Kate Berlant.

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