SAMANTHA HALE: Girl Uninterrupted

Lance Tooks Sketch
Illustration: Lance Tooks

Samantha Hale’s first comedy album I’m Only Happy When It’s Raining Men dropped in February and quickly went to Number One on iTunes.

“I worked my ass off for that,” Hale said. “I spent more time promoting it than I did recording it.”

No stranger to the public eye, Hale is granddaughter to the late Alan ‘The Skipper’ Hale jr. of Gilligan’s Island fame. She sat down after a couple gigs in L.A. – and a socially-distanced horseback outing to discuss her history, her path as an up & coming comic, and drawing the perfect horse.

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Earlier today I ran into a friend who’s a Vietnam vet and he said: ‘ask her about ‘The Lobster Bucket…’

The Lobster Barrel!

And a few other people shared ‘I remember Alan Hale’ stories. And I thought: OK, one, everyone apparently has a story about your grandfather, and two, this restaurant he had must’ve been later in his career.


So that said, what stage is ‘I’m Only Happy When It’s Raining Men’ for you?

I think it’s the beginning of a new stage. The first was ‘I wanna be a good comic.’ I wanted to actually know what to do with an audience. I started about nine, ten years ago. I took some time off because I was doing documentary stuff.

I never intended to be a comedian. I thought I needed to be an actor because that’s what my family did. I thought if I’m going to have any value as a human being, I needed to carry on the family name. I really put that pressure on myself at a young age. Doing acting, I’d get little things here and there, but I was frustrated because so much of that is out of your control. You can’t help what you look like, or if you remind the director of an ex-girlfriend, or you’re too tall or you’re too fat. And there were so many women my age doing the same thing.

So one day a friend asked ‘do you wanna come to The Women of Chelsea Lately at the Laugh Factory?’ And I was like ‘sure, sounds fun.’ And I sat there thinking ‘they’re so empowered. They have opinions. They’re not afraid to be who they are.’

We talked to Natasha (Leggero) after the show and she told me about ‘Pretty Funny Women.’ And I was like ‘OK, I’m curious.’ And whenever I’m curious or scared of things I tend to dive right in.

First show I did was at the Comedy Union here in Los Angeles. Dawn Wells came and sat in the front row. I’ll never forget that. She sat right in the front. Dawn is like my adoptive grandmother. I adore her. A mutual friend, Bill Funt, his dad was Alan Funt, somehow connected all the family members from Gilligan’s Island on Facebook and on email. He kinda introduced us all to one another. I’m still friends with Russell Johnson’s daughter, Kimberly. I know Bob (Denver)’s wife. You know, we all kinda chat.

So with comedy, you wanted to dive right in. Were you also that kind of a kid?

Oh yeah. If I wanted to draw something I’d work on it until my Dad literally took away my art book. ‘Hey hey hey you’re freaking out too much about this, it looks great.’ And I’d be ‘but this color isn’t right, or this outline, I didn’t draw the horse, it doesn’t look good enough.’ I’m such a perfectionist – which is weird because my parents didn’t really force anything on me, I forced all that stuff on myself. Maybe when you’re not pushed into anything you tend to want to do it more.

Samantha Hale Horse

I had a piano phase. I kinda taught myself. I inherited a piano and I’d already played other instruments so I was familiar with scales and things like that. But my parents never made me take lessons.

And maybe that’s what happened with comedy. I’ve always admired strong women. When I was a kid I wanted to be Xena Warrior Princess. So when I see strong women that are comfortable in their own skin… that’s what I felt like I wasn’t at the time.

Was there a transition, like a door you passed thru one day and went ‘oh, that’s what that’s like!’

Someone told me when I started: ‘you’re not gonna be good at all until you’re five years in. And you’re not gonna really be good until you’re ten years in.’

Like there’s a hard and fast rule.

There isn’t. But I understood what he was saying. The two year mark is when you get that false sense of ‘I’m awesome.’ You start doing shows, you have a strong seven minute set, you do ten minute sets, and you start thinking ‘ahh, I got this.’ And then you get your butt kicked at five years in because you start doing bigger gigs, doing longer sets, maybe you start traveling. But if you have ten minutes in L.A., you have three or four minutes in the rest of the U.S. A lot of it is very regional.

So I really had to find out who I was. What my point of view was. And that’s the hardest part of doing stand-up, finding your point of view.

Comedians are often labeled with a ‘brand.’ Kinison was ‘loud,’ Laurie Kilmartin could be called ‘Mom-Com.’ Does your comedy have a ‘brand?’

The other day someone in the LGBTQ community called me the Chelsea Handler of West Hollywood. A huge compliment. I’m a straight woman who lives among the drag queens. It’s given me such insight, being the straight girl at all the drag shows and gay bars. Gay men love a confident woman.

The change came when I started to get a little more confident. When I first started I was very self-deprecating, like ‘oh hah-hah, look at this thing I’m not very good at.’ I would smile. I’d want people to like me.

Then I started writing jokes that were a little darker. A little edgier. And I didn’t really have the balls to do them. As I got older I think my sense of humor got darker.

Do you think that’s who you really are?

Yeah. Life has handed me a lot. What really brought me to another level was losing my Mom. I hate to say it but when you go through something as painful as that, what’s the worst that’s gonna happen at a show? What, you’re not gonna like my joke? I don’t give a shit, I just watched my Mom die of cancer.

And when you have that freedom, you can do more because the audience trusts you more. The more confident you are… I have a few jokes where I’ll just stare at people until they laugh. But when I first started I couldn’t do that. ‘Oh no, they’re gonna hate me!’

Do you crave the moment you go on stage?

Depends on the day. There’s a time when my personal life is overwhelming and I gotta go out there and.. it takes a lot of energy. Every time I walk up to the stage and I have the mike in my hand, I’m fine. I’m ready.

Have you been missing that moment during Covid?

This entire time has been an emotional ride for all of us. I think the simplest way to put it is good days/bad days. There are days I think ‘OK, this is a chance to develop other parts of my life. Work on my house. Plant my garden. Regenerate my mind and not be in go-go-go mode all the time. But then there are days like ‘everything I’ve done with my life I can’t do, so who am I?’ I know a lot of comics who’ve had an identity crisis because of this.

When I miss comedy and I feel as though I don’t have an identity, I focus on making memories. I wanna be on my deathbed, whenever that’ll be, thinking ‘remember that time…’ and I’ll say ‘oh yeah, I did do that!’ I mean, how many people can say they jumped into shark infested waters and swam on top of a whale shark?

Down there (Cancun) I managed to get on the wifi and still do a show. And I had a whole new ten minutes of stuff to talk about, because I was doing something that didn’t involve sitting in my house. So now that I have this new stuff to play with, I really wanna do a show. I have these new toys. That’s how I think about jokes sometimes, they’re like toys and when you get a new one, you just want to play with it all the time.

I know comics who just eat, breathe, sweat comedy. And that’s amazing. But I wanna have a life, too. Losing my Mom, everything changed. We’re so hard on ourselves.

‘Drawing the perfect horse.’


Is that where you are with ‘Raining Men?’

I’m so proud of this album. We went to record an album four years ago and I’m so glad it didn’t work out. I thought I was ready. But I was really stressing to get fifty minutes of material. And now I record an hour fifteen and cut it down, cut it down.

The first album, I was booked in Louisville, Kentucky. Should’ve been perfect. Except the manager booked me during the Thunder Over Louisville festival, the precursor to the Derby, so the whole town was out watching fireworks! No one at the club.


You learn from bombing. You don’t learn from doing well. It feels great and it’s fun, but you learn more when something doesn’t work. Was it the set-up? Was the punch not strong enough? Is it just too dark, am I the only one who thinks it’s funny? If I meet an artist – singer, songwriter, actor, if they think everything they do is great, chances are it’s probably not.

Does it weigh on you, or did it early on, that people were going to judge you based on the family name?

I’ve only seen it as a positive thing. After all there is no other comic out there that can do a joke about The Skipper being her grandpa. That’s mine.

Unless Dawn Wells’ daughter gets into the business.

She doesn’t have any kids! I’m fine. Bob, I think his son Patrick is in stunts. Special effects? Tina has a daughter who I believe is a writer.

Samantha Hale Hamburger Mary's

So for you, the family ghost isn’t back there, nudging…

I don’t feel that pressure. Which is weird, because I put so much pressure on myself. Maybe when I was first starting I felt that. But now I’m really happy with who I am.

Speaking of all things ocean, where did your love of marine biology come from?

As a kid I was drawing orcas and whales and dolphins. I was part of the Free Willy fan club. I wanted to be a marine biologist. A dolphin trainer. But then I found out how much schooling was involved and how little money they made and I was like ‘I wanna be an actor!’

Dad was a big bodysurfer. He’d take me to Gladstones on PCH. That was the big special treat, we’re gonna go eat on the water. And my grandfather, along with playing The Skipper he did actually love being out on the water. We buried them both at sea. Neptune Society. It felt right.

One day, I’d gone to the beach, I was walking up and down by myself a while and I said ‘I just want to know that you’re alright.’ Ten minutes later I see something wash up on the edge of the water. If I see trash along the beach I’m going to pick it up. So I go over and it’s one of those little happy-face balls you put on your antenna. You want an answer, you get an answer! There are times when it’s not a coincidence. That was really specific. 

I’m not a ‘sit at the beach and get a tan’ type of person. I wanna go out in it. ‘C’mon, let’s go see!’ I’m weird that way. We all have our different fears, our different level of adventure. I show people video of me swimming with a shark and they’re like ‘are you insane?’

But then there are people who’d never do stand-up.

The title of the new album came from a song –

Two songs! They (Garbage) were the first band I ever saw – KROQ’s almost-acoustic Christmas. Twelve bands on the line-up. They were one of the first out. Right after No Doubt. Shirley came out, she was this force to be reckoned with. My Mom bought me their album for Christmas. I listened to it on a little boom box.

Later, turns out one of my friend’s brothers is one of their managers. At first it was ‘oh I’ll get to get a picture and say hi.’ Then I struck up a friendship with Duke (Erikson, the guitarist) and we’re talking at a show and I said ‘I’d really like to go see another show on this tour’ and he’s like ‘let me know.’ So now I plan, I can do stand-up in whatever city when I know they’re going to be in town. I was in Scotland with a friend. They were playing the day I landed.

Shirley’s one of the most genuine people. I have nothing but good things to say about that woman. She actually cares about people, she remembers you, and what I really admire is her taking her platform and raising awareness for LGBTQ rights. She talks about politics. Women’s rights. She sees what’s going on in the world and really wants to help.

How does music play into your creative process?

I write about things I’m passionate about. I love Rob Zombie. I’ve got a joke about his beard, another about a dream I had where he goes down on me. In my dream I was like ‘no Rob, you’re married!’ And when I woke up I was like ‘what the hell, did I just cockblock my own wet dream?’ I think I’d been watching one of his movies before I went to bed.

I’m still very stuck in the 90’s. I have a lot of 90’s references and 80’s references cause I just generally like older movies. And I love the 90’s musically. I have fun telling these jokes then harassing the twenty year-olds in the audience. ‘Oh, you don’t get this.’ I have a Nirvana joke about Kurt Cobain and they had no idea who I was talking about.

Ever thought about being in a band?

I had a bass phase, I had a cello phase. I’m not musically inclined. I think keeping time is a nightmare. I’d love to be a singer but I have this insane fear of singing – I think I must’ve been a really bad singer in a past life and got stoned to death for a bad performance.

I won’t even do karaoke. Nope. Don’t wanna do karaoke and I don’t wanna jump out of a plane. Some people love that. But some people won’t go cage diving with great white sharks. I loved every second of it.

You recently traveled –

I got a lot of material going to Mexico. It was new and fun and exciting. A different culture. I learned a lot. If you’re a comic and all you do is go to comedy shows, what are you going to write about? People want to hear about your personal adventures and stories and weird memories. Things people say to you. Especially when you’re a woman. Traveling alone. During a pandemic.

I caught my first in-person laugh from our tour guide and I went ‘oh, this is what it’s like to make strangers laugh. Still got it!’ And all I had to do was go balls deep into the jungle.

I went camping in Tahoe with a wonderful group. I happened to be the only straight one but whatever, I’m used to it. It’s fun. They did make fun of me because I tried to bring some healthy snacks. They’re like ‘these chips are made of kale, what are you doing!’ I brought all these cans. I mean, I’m not a camper, that’s what you’re supposed to eat, right? Nope! They brought a full kitchen. We had steak. We had chicken. They do not play around. I was very impressed. We had margaritas. One of my friends brought this powder, you throw it on the fire and it makes a rainbow. The best part was to just break that Groundhog Day effect.

Back when you were getting started, did you have any kind of secret to improving? Did you film yourself, record yourself?

I used to record everything all the time. Now I’ve become really disciplined. If I’m trying new material, if something works, I’ll write it down the second I get offstage.

Comedy is a dialogue. You’re not up there giving a speech. You’re not talking at people, you’re talking to them and with them. The whole excitement for me, especially now that I’ve been doing it a little bit and I’m comfortable, the most fun is doing crowd work. Telling jokes then having to deal with it if it doesn’t land, having to play with people, hearing their stories. A lot of my material I write on stage.

There are times when you’re hyper-connected and it’s beautiful and they’re so in that moment and you’re on fire. And then there are times when you do your opener – you want to open strong/close strong – and your opener doesn’t hit and you’re like… well, they don’t like that so let’s try this. Sometimes you keep it internal, but you’re always listening to the room.

Are you a big re-writer?

I’ve got notes of jokes going back years. Sometimes they come to you, and sometimes you’ve got this amazing set-up and you want it to work so bad… but you just can’t find the punch for it. Years later, you write something that finishes it. The idea is to get up there and work your ass off to make it look like you just thought of it.

A lot of comedy is in-the-moment riffing. Some comics, it’ll seem like they’re just talking to you, they just thought of this and you’re like ‘wow, it’s like we’re just sitting in his living room and he’s just shooting the shit with us.’ Then you see the ten o’clock show and he does the same thing and makes it look like he just thought of it.

Are you thinking funny all the time?

I’m not one of those comics that doesn’t turn off. When I’m not working I’ll naturally say things that are funny but I’m not trying. If I go out to a show I’m happy to just hang out. I don’t need to be the center of attention.

I’ll be writing jokes that I think are just ‘meh’ and I’ll think ‘whatever, I wrote it, might as well try it’ and it kills. And I’m like ‘really?’ Then I’ll write something that I think is so smart, so funny, and the audience doesn’t get it. And you’re frustrated. Sometimes it’s the wrong crowd. Sometimes what you think is funny they might not understand. It’s all about gauging the temperature of the room.

When you’re a new comic and you only have ten minutes you can’t change your set right in the middle because they don’t like it. But now, I have enough material that I can say ‘OK they’re not going for this, I better..’

At what point did it start to appeal to host and produce?

A lot of comics, when they’re new, they’ll do open mikes. And that kind of gets you in. But hosting is a different skill.

You’re getting up there, the audience is ice cold, you don’t know what the room is like yet. People are still being seated. They’re ordering drinks. A lot of times they don’t even know you’re a comic. They’re not drunk yet, so they’re not loose.

Talk about the Monday night thing with Micky’s in WeHo.

I have to say, as I started working with drag queens, their sense of humor – we just rip the hell out of each other. Constantly. It’s our way of showing affection. I was freed with how much fun they’d have with that kind of humor so I started writing that way. Edgier. I started working in more gay bars. The crowds weren’t expecting a straight cis woman. So I had to get their attention. You had to be fearless. And once you get their respect, they’re the best audience ever.

Samantha Hale Standup

A friend of mine, one of the queens from ‘Rupaul’s Drag Race’ worked (at Micky’s) and one of the managers said ‘I think we wanna bring in a show for happy hour.’ And my friend said ‘hey, you’ve got a comic right here.’ And they were kinda like ‘ehh, I don’t know.’ But I wrote up a proposal, really convinced them, and yeah – every Monday for four years. Right place, right time.

Then word just got out. I hosted. A lot of comics don’t like hosting. It’s that much more work.

Does hosting limit your time to write new material?

Hosting at Micky’s, a lot of the same people are there every week. It forced me to come up with new stuff to talk about. But because it was my show, the pressure was kinda off. If I do new jokes and it doesn’t land, who am I gonna fire? Me? I’m not gonna fire me.

Got a favorite heckler story?

The first time I tried to record an album was in Kentucky. And there was this party of twenty in the back. And they just hated everything I did. I did a birth control joke. Dead silence. And from the back of the room this woman says: ‘girl, you trippin!’ She was so loud, and I was so shocked by it I think I said ‘yes ma’am you’re right, I am in fact trippin!’ And it clicked in my head ‘OK, well, they already hate me, so I might as well do whatever I want now.’ Another reason I’m glad that album didn’t work out.

Then I did a joke about Kim Kardashian having sex with a black guy and they loved me. Oftentimes, I think an audience senses my attitude’s changed. I have nothing left to lose. I’m no longer trying to impress you, so why not. And suddenly they trust me.

You do a lot of jokes about exes. Ever had an ex show up at a show?

I had a guy I was dating a while, he approached me after my set. One day we were out having drinks and he asked me about this joke about my ex-boyfriend’s penis. And he said ‘is that joke true?’ And I’m like ‘yeah’ and he said ‘you’re actually talking about a real guy’s dick?’ And I’m like ‘yeah…’ And he got really upset! Like ‘well I’m never gonna show you my dick.’ And I’m like ‘well first off I never asked and second, what’s wrong with it?’ All of my jokes are based on truth. Sometimes they’re exaggerated, but that’s the nature of comedy.

The funny thing is I had a video clip of that joke posted online, and some of my friends who are still friends with my ex reposted it. Of course it got back to him. And he messaged me: ‘hey, Teatherball.’ Which is the punch line. He thought it was funny.

Is clean comedy a bigger challenge?

Yes. And there are different levels of clean. There’s PG-13 clean, there’s corporate clean, there’s squeaky clean. Some places say ‘you can’t use any swear words, no offensive content, no sex.’ Jokes that have no shocking content are harder to write.

There’s a joke structure we teach (at Slay). Some people will fight you on it, but they come around in the end. Figuring out who you are as a comic takes a lot of time. My point of view when I started is very different than where I am now. But I got more in tune with myself. I know what I like as a comic, what makes me laugh.

Beverly Willenberg Artist, Samantha Hale Sketch
Credit: Beverly Willenberg

When you’re onstage, do you ever find yourself having an inner-dialogue?

There are times you’ll go on autopilot, and halfway thru you’ll say ‘I don’t wanna do this.’ I’ve literally said ‘ah, I don’t wanna do that joke.’ The audience, they’re really smart, they can tell when you’re in it and you’re not. If you hesitate – they don’t trust you and they’re not gonna laugh.

If you go in there with a new joke and it doesn’t work and then you get uncomfortable and you feel terrible and you beg for their approval? It’s not gonna work. But if you’re OK with whatever the outcome is, it’s still gonna be fun.

I love seeing people bomb who don’t care and are able to recover. That’s the most genuine you’re going to see a person.

One of the best examples of that was Johnny Carson. He did this five minute monologue, not a single joke was hitting and he started commenting on how unfunny it all was and it was the funniest thing you’ll ever see. He was so real in that moment. He knew what was going on and he didn’t try to fake it.

Sometimes you’ll see people when their joke doesn’t work they’ll talk louder or faster. It’s just not going to work. The audience will cramp up. They’ll tune out.

We tell the new girls that come in to take the class, if something doesn’t work – just say it. If you forget your joke say ‘I forgot my joke!’ and you’ll get a laugh. You’ll get a laugh if you tell the truth.

I’m doing comedy more for me now. I’m more open to failure. Nothing is scarier than watching your mom die of cancer. Nothing. And I’m grateful to my mom for giving me that gift.

One of my writing partners, Anna Valenzuela, lost both her parents before I lost both my parents. And she told me ‘your humor’s gonna get really dark really fast and people aren’t always going to know what to do with it. And that’s OK. Speak your truth.’

And the album captures that.

I’ve got to this place where I’ve just let go. I feel more freedom with it now. I’m not a larger-than-life character. I’m a bit more…


Yeah! That would be a big compliment.

Samantha Hale’s new album ‘I’m Only Happy When It’s Raining Men‘ is available on iTunes, Spotify and Apple Music.


MATT McGEE lives and writes in the Los Angeles area

LANCE TOOKS is a former editor at Marvel

BEVERLY WILLENBERG is a Los Angeles-based artist

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