Ep. 024 – Wedding Entertainment, Caricatures by Alyssa (Tanner)


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Bringing a non-traditional, live wedding entertainment to guests, Alyssa Tanner is the beauty and brains behind Caricatures by Alyssa based out of Rapid City, South Dakota.

Meet the Wedding Entertainer

Alyssa Tanner received her bachelors degree in illustration from Indiana Weleyan University and returned to her home in the South Dakota Prairie where she’s been serving the community and honing her craft for the last decade.

Inspired by the many faces she gets to meet and draw, Alyssa’s goal is to:


Follow her on:

Other Media Appearances

Black Hills Women’s Magazine, Feature Artist, 2020 / Read here

Lay the Course podcast guest, 2020 / Listen here

Photo by Henry Roy Photography


INTRO: You’re listening to The Pulse, an artist podcast based out of Rapid City, South Dakota. Let’s chat about all things weddings!

I’m your host Sarah Grassel. Mother, wife, and entrepreneur.

I am a full-time destination and travel wedding photographer/videographer with a passion for telling stories through photo, video, and writing.

I’m also a published writer in several South Dakota magazines including Black Hills Lifestyle, Unveiled, Siouxland Woman, Motor Market, Black Hills Woman, and a few others. (Read more about me).

Thank you for joining me and for tuning into the show. Be sure to like and subscribe, and leave a comment on the episode to share your voice!

photo provided by Alyssa Tanner

Host: Welcome back to the podcast. Today I have Alyssa Tanner with Caricatures by Alyssa. I’m really excited for this episode to be released… a little background – we’ve tried this once or twice, no fault to Alyssa, I have had some technological issues. So thank you for your patience and for re-recording time and time again.

Alyssa: Hey Sarah, it is great to be back. I’m so excited for today.

Host: I feel like we’re really getting to know each other.

Alyssa: We are! Oh my gosh, we’re like best friends now.

Host: I know, we know so much about each other. And you know all about my lack of technology skills now.

Alyssa: Hey, it’s okay. It’s all a process; we’re all learning.

Host: I appreciate it. But let’s go ahead and dive into your background: a little bit about yourself and let’s go from there.

Alyssa: Alright, let’s do it!

Host: So… where are you from?

Alyssa: I am from Rapid City, South Dakota, but I was born in Arkansas.

Host: Oh, I didn’t know that.

Alyssa: Yep! We didn’t talk about that last time.

Host: Learn something new every time.

Alyssa: We moved here in 2000 with my family for my dad’s job, so I was nine at the time. I basically consider the Black Hills my home.

Host: Yeah, and so you do caricatures! Let’s tell me a little bit about your educational background and how you came to love and pursue characters as a as a career.

Alyssa: Absolutely, so I went to Indiana Wesleyan University. I got a degree in illustration. So that’s more like children’s books, illustrating background. So like, art that tells a story is basically what illustration means. While I was there, we had people come recruiting for one of the amusement parks that was close by on that side of the country. They were with Cedar Point, and they did like a little demo. And they’re like, “Yeah, you just apply and work here. And it’s a summer job.”

Host: Yeah.

Alyssa: I’m like, “What!? That’s how this works?” Because I would always see these people drawing caricatures. You know, like, when we would go on a trip, and, you know, they’re on like, a boardwalk somewhere just drawing pictures. I’m like, “Wow, that’s so cool. But it’s like, how do you even start?”

Host: Right.

Alyssa: But yeah, so they came and it was like, a paradigm shift. Like it was so eye opening. But I did apply. You know, I went home, and I practiced what they taught in their little 15 minute demo that they did in our class. And then I went and I applied and part of the interview was drawing one of the people that was interviewing you.

Host: That’s cool!

Alyssa: Yeah, yeah. So no pressure. But it was it was really fun. They weren’t like super harsh or anything like that, because they hadn’t even like trained right me yet or anything. But I did get the job. I was hired on the spot. However, it didn’t work out for me to work there all summer, because it was very far away from South Dakota.

Host: Right… where was that?

Alyssa: Marion, Indiana. And then Cedar Point is somewhere around that side of the country. I’ve never actually been. But it was just kind of like an eye opening experience for me. So then it was just kind of rolling around in the back of my head. That summer, I ended up getting a job babysitting. I went and took these kids to Storybook Island, which is a children’s Park here in Rapid City. There was a gentleman there drawing caricatures. I just said to the kids, I was babysitting and I was like, “Hey, you guys just hang out over here for a minute…”

Host: You do you, and I’ll do me.

Alyssa: “I’m going to talk to this fellow over here. I gotta go see what he’s about here.” You know. I went up to him, and I introduced myself and I said, “Hey, could you give me any pointers? I’m super interested in drawing caricatures.” His name is Ted, the man that was drawing characters at Storybook Island. He was so nice. You know, he was thrilled that I wanted to learn from him. He had a daughter that’s about the same age as me, and she couldn’t be any less interested in caricatures.

Host: Polar opposites?

Alyssa: You know, you don’t appreciate what your parents do. I think that’s just kind of a given you. Yeah. What your parents do is always uncool.

Host: That’s why my dad is the IT guy, and I know nothing about technology.

Alyssa: Right! Yeah, see you get it. But yeah, so it was kind of that situation. So he was like, “Oh, my gosh, sit down. Let me show you some things.” You know, he just has the heart of a teacher. You know, and he just impacted my life so much. His name is Ted Craft. He’s from Arizona. He ended up moving back to Arizona. But that’s kind of how I got my start drawing caricatures.

Host: Yeah, so you started just at Storybook Island, really.

Alyssa: Yes, so he moved back to Arizona and then he gave his account with Storybook Island to me. Then, I was able to work with them and draw summer caricatures. So it started out as like a summer job when I was home from college. Then, I needed an art internship. So I was like, can I just work for myself? And my professor was like…

Host: They let you do that?

Alyssa: My professor did! He’s like, just keep a journal of everything you do every day. Because I had to pay rent for the space, had to keep track of taxes, I had to keep track of like, customer service situations keeping track of my supplies…

Host: So literally a journal of everything.

Alyssa: Yeah. I mean, like, just my process of learning how to run my own business. Yeah, it was fantastic.

Host: That’s really cool. So that’s a true field experience.

Alyssa: It really was, and then guess what? Ten years later, I’m still doing it.

Host: Are we coming up on it, is this your ten year anniversary?

Alyssa: I started learning in 2011. So that was kind of my learning summer, and I would work with Ted. Then he would also draw at a street festival called Summer Nights, where we just set up on street and draw people. We would work together because there would be so many people.

Host: Do you still do it at Summer Nights?

Alyssa: Not really. It’s one of those things where it was a good experience. I did it for a couple summers; it was a good experience. And then they kind of changed things around with like the kids street. So then they didn’t have the kids street. But then there was another street right next to it that was also doing the same thing, but it was different people and different rules. And so it was just very complicated. So I was like, ehhh…

Host: We’ll just stick to Storybook Island.

Alyssa: Just stick to Storybook Island, yeah.

Host: Yeah, for sure. So how did your career kind of go and develop into the wedding scene?

Alyssa: So it definitely chose me. I was drawing caricatures at Storybook Island and a bride contacted the office and said, “Hey, can I get the caricature artist’s info.” I mean, this was like, before I even had like business cards. I just kind of did it as a summer job while I was working, you know, illustrating children’s books and things like that. But yeah, Storybook Island gave her my phone number. And she called me and was like, “Hey, I want you to draw at my wedding reception. This would be so cool.”

Host: It’s definitely unique.

Alyssa: So yeah, so it definitely chose me. And that’s how I got started with the wedding niche.

Host: You know, caricatures are so different than any other live artists, I think at a wedding. Because most of the live artists that I’ve seen around this area, you know, they’re setting they’re setting their equipment up… they’re painting or they’re drawing, you know, one scene from the day.

Alyssa: Like a fine art wedding painter, right.

Host: Yes. But you, you’re giving something to anybody that comes to you, like a gift to bring home with them to commemorate the occasion.

Alyssa: Yes! So what I’ll do is set up my easel, and I’ve got my spare paper and markers and stuff and probably get a drink. But yeah, and then the line just starts. I, you know, draw everyone with their big head and little body. It takes me about three to five minutes per person. I’ve been called the human photo booth, because that’s basically what I do. But yeah, everybody goes home from the wedding with a really awesome keepsake from the night and we can even do you know, we could put the the date and your names on the bottom as well.

Host: Do you do like a custom background or paper?

Alyssa: Yeah, so that’s like a custom paper. I would print that ahead of time on on all my paper. You know, like: Joe and Alex 2022. And then maybe something that represents their theme. You know, like, if it was in the fall, we could do like some leaves or roses or you know, just something that kind of hints back to the their interests?

Host: Does the couple get a copy of each of the characters draw? Or is it just the individual?

Alyssa: So I have been asked that before, and I try to take pictures in the middle of every single picture that I do. So I “Okay, hold up your picture!” and I take the picture holding it. But depending on how fast the line is, I just got to keep drawing. Because that’s ultimately what I’m there to do is provide that entertainment. However, I have had, like a dedicated photographer or cell phone photographer, stand behind me and take pictures of every single one as well. But yeah, I don’t have a an extra person that that comes and photographs, everything.

Host: That’d be pretty cool.

Alyssa: It would be really sweet. I don’t know how to price that though.

Host: Yeah, when you add a-whole-nother person, yeah…

Alyssa: Yeah, so I could just grab a friend and say, “Hey you’re gonna be here for the next hours taking pictures.”

Host: Yeah! You’re my new friend, my new buddy.

Alyssa: Exactly. Which I have done and it works out great.

Host: Well I think, like you said, it’s a really great entertainment for guests. Because a lot of the times, even at my own wedding, I don’t think there was anything. We didn’t have a photo booth, we didn’t have a kid’s corner, and it’s something that kids can enjoy, too. If you have a kid friendly wedding.

Alyssa: Absolutely.

Host: Maybe they’re just gonna sit there and watch you! It’s even entertaining to watch you do it.

Alyssa: Absolutely, I usually have a crowd behind me. I was – this one was a birthday party – but this lady sticks out in my mind. She was hilarious. She was like, “Oh my gosh, okay, draw this person, I’m wanna see what they look like.” And then, you know, if there was like, one person in line, she would make sure to get another one. She’s like, “Okay, you’re gonna be next.” She would queue everybody up there for me. So it was really fun. It was a smaller group, too. So she’s like, “Okay, I’m gonna see what everybody looks like in her style,” because this is just she was just so amazed.

Host: It is so fun. Because you can capture their face but you also kind of…

Alyssa: Yeah, so that’s the thing about caricatures is you know, it’s not a photorealistic drawing of somebody, but you’re capturing their personality and their essence.

Host: Yeah, that’s a great way to define your style.

Alyssa: Yeah. So it’s just really funny, because it’s just something about being in that person’s presence, seeing them face to face, and then drawing them from life, in three minutes!

Host: And with weddings, not only do you provide the live entertainment there, but you also offer to pre-draw or illustrate the couple as well. Can you talk about that a little?

Alyssa: Absolutely. So I also do digital caricatures. I take commissions from all over the world where people send me photos. The unique thing when I do weddings, is the bride and the groom will send me you know, pictures of their faces, pictures of what they’re going to wear, and then I usually have the bride send me like a Pinterest photo of what she wants her hair to look like. Then I illustrate it. These take a lot longer because they’re more detailed and in color. They’re like a painting almost, by the time we’re done, but I do it digitally. But yeah, and then I printed out and I bring it to the wedding before anybody has seen like what the bride looks. So it’s just really cool.

Host: Do you do like a special reveal with the couple or…

Alyssa: I usually send it to the bride ahead of time in case they need any edits.

Host: Gotchya.

Alyssa: But it’s definitely a big surprise for everybody else when they come. I usually set it up on the gift table or somewhere by where I’m drawing caricatures. But everybody like just comments on it throughout the night. “Wow. That’s amazing. How did you do this?” I’m like, Well, I did it a couple weeks ago beforehand.

Host: Want one for your Christmas card? Here’s my info!

Alyssa: Exactly!

Host: Want one for your child’s birthday party? Here’s my info!

Alyssa: Yeah, senior portraits, Mother’s day, Valentine’s day… I do it all.

Host: Oh yeah! I forgot you’ve also got a special for Valentine’s day coming up.

Alyssa: Yeah.

Host: Well this episode will be out before then if you want to give a shout out?

Alyssa: Yay! I’ve got a few spots left. I probably have about five spots left?

Host: Probably not by the time this episode comes out, but…

Alyssa: Yeah, going quick! But yeah, that’s kind of my my two caricature styles is the black and white drawings that I do in like three minutes. Then there’s the digital ones that take me you know, anywhere between three to five hours depending on…

Host: Well, I was going to say, doesn’t it depend on like how many people and whether or not they want a custom background or if you’ve already got one set up?

Alyssa: Yes

It’s like magic on a page…

Alyssa Tanner

Host: Yeah, a lot of dedication and time in your craft for sure.

Alyssa: Oh, absolutely. But it is so much fun. And it is so rewarding!

Host: What’s your favorite part of both A) just characters in general and B) being a part of the wedding industry?

Alyssa: So I would say, A) drawing the caricatures, what’s my favorite part?

Host: Yeah.

Alyssa: Okay, um, yeah, double questions!

Host: I know, I should really just break them apart.

Alyssa: Nah, you’re good. That’s why I asked for clarity. Um, I would say my favorite part is the reveal. So like when I’m drawing all those quick pictures of people and I turn it around really quick, you know, I’m always looking right at their faces. Um, yeah. A lot of great reactions.

Host: A lot of shock? Just because they’ve never seen something like that?

Alyssa: Yeah. You know, it’s crazy. Most of the people I draw have never had a caricature. Yeah. I mean, part of that is because of the area we live in. You know, whether people travel a lot or not, you know, it’s definitely something you see at like theme parks and big attractions.

Host: Well, we don’t really have any theme parks.

Alyssa: Yeah, we don’t really have that many here. So yeah. So it just depends on how much you get out. I mean, we’re not quite in the middle of nowhere, but there’s not like Disneyland next door.

Host: Right, or six flags…

Alyssa: Yeah, all that good stuff. Um, but yeah, so the reveal is really cool. Um, because a lot of people it’s their first time or maybe they were nervous. I’m a nice caricature artist. I make you look good. Um, but yeah, I definitely have a cute style. But yeah, that’s the really cool thing about caricatures is they all look different, but they all look like you.

Host: Yeah, for sure. And then be what’s your favorite part of the wit being part of the wedding industry?

Alyssa: Oh, everything about weddings is just fun to me.

Host: I love that you say that with a smile on your face. So sincere.

Alyssa: I love it, though. It’s true. I really have the best gig when it comes to the wedding niche. Because I just set up and I have fun. Yeah, that’s literally it.

Host: Well and you get paid to be there, so you get paid to do something you love.

Alyssa: Exactly. But I get to hang out with lots of fun people. You know, like little kids, I like to ask them questions. Older people ask me questions like, you know, just a lot of great conversations and getting to know people’s friends and family.

Host: Right? What’s the longest you’ve been at a wedding or the shortest you’ve been?

Alyssa: So I have a two hour minimum. So two hours would be the shortest. And then the longest I’ve done is… gosh, was I there… it was a five hour wedding. They booked me for five hours.

Host: Oh wow!

Alyssa: Yeah. It was a huge wedding.

Host: That’s a long reception.

Alyssa: It was. Um, so I did six hours, no, I did five and a half hours. So I had a 30 minute break and then a few other little breaks sprinkled throughout.

Host: Gotta eat sometime!

Alyssa: Well not only that, but rest my hand mostly because it will get sore after drawing so fast for so long. And then it’s basically a road trip – you got to stand up and stretch your legs. Yeah, it’s like a good road trip for five hours. But yeah, so I do schedule like little breaks for myself. That’s usually written on my board. Just so guests know when I’ll be back and stuff.

Host: That’s smart.

Alyssa: Yeah, that was definitely the longest it I went all the way to Mitchell, South Dakota. That’s about three hours away. But yeah, the entire town was there.

Host: I feel like a lot of east river weddings are like that.

Alyssa: Yeah…

Host: I mean, my husband’s family is from east river. One of the weddings that we went to for his cousin, like the attorney general or somebody you know, really like high up in South Dakota politics or something like that was there and ended up staying at this rinky dink small town motel in Howard, South Dakota.

Alyssa: Yeah, what else are you going to do on a Saturday night there?

Example of Caricatures by Alyssa Providing Live Wedding Entertainment

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Host: But, yeah. I just love weddings. And I think like, it takes a special person to work in the wedding industry, though. Because you have to have a lot of patience.

Alyssa: You do.

Host: But you also have to have a lot of a lot of passion. And like you have to be there and keep people calm. And I don’t know how true that is for you, as a caricature, a live artist there, but as a photographer/videographer who helps like kind of run the show – it’s like you’re the one that’s gonna be maybe getting the bride water and making sure she’s sitting down before everything starts… but I think weddings are a lot of fun. And I don’t know, I see a lot of people that are getting burnt out, because of how many weddings there were this last year. So it’s really nice to like, see that you still have a passion and…

Alyssa: Oh yeah, and I mean, I don’t schedule a wedding every single weekend also.

Host: Yeah.

Alyssa: It’s definitely quality over quantity when it comes to booking weddings. You know? I think I did two weddings this last year, only two, where I had two events booked both days.

Host: Back to back?

Alyssa: Yeah, so like, I worked an event in the morning. I didn’t explain that very good. I worked in event in the morning for four hours and then I had like, maybe a three hour break. And then I went in worked another wedding.

Host: Yeah, wow. That is a lot. That’s a long day!

Alyssa: It is a long day.

Host: It’s really hard on your hand; you mentioned having to take breaks…

Alyssa: It is, but I do schedule massages and I tell them like, “Okay, you spend at least 15 minutes on that hand!”

Host: Do you get like regular hand massages?

Alyssa: Well, no. It’s usually like a full body, but when they get to my arms I’m like okay, focus on that. That’s a key point. Yeah

Host: That’s a key point, yeah.

Alyssa: Yeah, my hands are very important.

Host: Sure. We kind of talked a little bit about it because you’re about the only caricature artist, but what sets you apart from others in our area?

Alyssa: There’s just something special about drawing something on paper. Like, how many people do you know, that can just look at a person and just draw them?

Host: Right?

Alyssa: You know, I mean without spending a ridiculous amount of time on it. So that I think is just the appeal of it is… it’s like magic on a page!

Host: Magic on a page; that fits with your Storybook [work], too.

Alyssa: Yes.

Host: Or any fairy tale weddings – Magic on a page…

Alyssa: Absolutely. You know, or people that have like a goofy side. Oh, my gosh, it’s always a hit. I always have a long, long, long line.

Host: Yeah, I love that. Before we close out, I want to get into the overarching themes of the podcast. So let’s go over your definition of art.

Alyssa: So my definition of art would have to be art is a message, right? So whenever we’re creating art, we’re conveying a message, an emotion, a feeling, just something to put out into the world. And when caricatures are drawn, like at a wedding, for example, it’s a thank you, from the bride and groom… that you were there. So that would be my definition of art. It’s always a message.

Host: I love that. Well, and you mentioned at the beginning of the episode, that, like illustrations specifically is art of the story? Is that how you put it?

Alyssa: Yes, yeah. It is art that tells a story.

Host: Yeah, I love that. And then, what advice do you have for other artists?

Alyssa: So advice I would have for other artists… One is try lots of things. I tried lots of things. But yeah, definitely try lots of things. If you’re interested in it, figure it out. Yeah. How does it work? You know, I tried caricatures.

Host: You are never going to know until you apply yourself.

Alyssa: Exactly. Apply. Google it. You know, YouTube… there’s so many free resources out there for learning literally anything, so just try, research, explore. The other advice I would have is just ask.

Host: Oh my gosh.

Alyssa: Like, I went up, I literally went up to some guy I didn’t know. I was like, “Hey, can you give me some pointers?”

Host: That is my biggest struggle, always has been. I’m like such a non-confrontational person. It’s hard. Even if I have like a tiny like, asking where the bathroom?

Alyssa: Oh, no. Yeah, don’t be shy.

Host: I should definitely take that into [consideration] and really hold… maybe that should be my 2022 theme.

Alyssa: Just ask. Yeah, it’s great. Um, now there are better ways of asking that I have learned. I’m going to share that nugget. So asking someone that knows something you want to know how to do, but take them to lunch? or coffee? Preferably coffee, if you’re like a younger artist and don’t have a budget.

Host: …or tequila!

Alyssa: Or that, yeah, but asking someone to coffee, just to kind of learn a little bit about a topic that somebody else knows about. I have literally done this with people like last year…

Host: I think it’s someone very conversational.

Alyssa: Yes. Someone knew how to do something, I want to know how to do, and I took her to lunch. I’m like, “Hey, how does this work? Yeah. Tell me all about it.” You know, and I bought her lunch. But yeah, so that’s a really great way to learn how to do something. So if you have a business, like that’s also a tax write off, which is great. Because you’re educating yourself.

Host: Yep, save that receipt.

Alyssa: Yep, you’re educating yourself. So those those are my two tips of advice is try things and research it and then just ask for help. Ask how things work.

Host: Yeah, those are perfect. I honestly think that the asking is going to be my my personal goal this year.

Alyssa: That’s awesome.

Host: Thank you for that inspiration.

Alyssa: Yeah, absolutely. I mean, there’s all kinds of people that know how to do things we wish we could do. I wish I could be like so and so… well, take them to coffee.

Host: Yeah.

Alyssa: Figure it out.

Host: I love that. And then just give a quick shout out to your social medias and website. I will have those in the show notes. But just if anybody’s listening wants to know where to find you. Let’s give a little shout out!

Alyssa: Absolutely, you can find me at CaricaturesByAlyssa.com, Caricatures By Alyssa on Facebook and Caricatures by Alyssa on Instagram.

Host: Awesome. Thank you again for being here and for recording with me. Round three. And I’m so excited to release this episode, as well as the others in the future.

Alyssa: Thank you so much, Sarah. It’s been a pleasure. Thank you.

***this is not an exact transcript.*** Recorded  | Released 01/29/2022

OUTRO: Every artist lives in their work.

Pulse is defined as an arterial palpation or a strong regular beating or throbbing. In this podcast, discover artists in the Black Hills who uncover new techniques and live passionately for their work to bring brides and couples something beautiful for their special day.

This podcast started as a connection with artists in The Hills and now focuses on wedding related artists and vendors. From florists to stylists, bakers, and more. Thanks for tuning in!

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