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Tristan Prettyman Rides the Crest

Updated: Oct 30, 2021

Tristan Prettyman

Tristan Prettyman

Tristan Prettyman

Rides the Crest

by Jay S. Jacobs

Tristan Prettyman would rather be surfing.

Not that she doesn’t love her current career as a singer/songwriter, but she might just be talked into chucking it all for a guaranteed endless supply of great waves.  She has been on the beach since she was a little girl and surfing is one of the great passions of her life.

That would be our loss, because her debut CD twentythree is a truly individual statement, a quietly devastating and exhilarating acoustic celebration of being alive.  The disk shines with wonderful guest appearances by G. Love (who also appeared on her well-respected indie debut EP Love), Jesse Harris & Lee Alexander (both best known for their work with Norah Jones) and Prettyman’s folk-rock-hero boyfriend, Jason Mraz.

Despite suffering from a nasty, lingering cold, Prettyman sat down with us to chat about her album, her career, her life and the waves…

How did you originally get into music?

Kind of by accident, actually.  The way I remember it was that we had a guitar in the house and I would play around on it, but I couldn’t really play.  Then, just over maybe a span of like five years, I would just keep going back to it.  It was something that I’d pick up, put down, pick up, put down.  Eventually, it kind of stuck.  The more I played, the more I learned.  Obviously the more songs I started writing.  It’s such a gray area for me.  I just remember all of the sudden I was writing songs.  I was comfortable.  I would record myself and go, God, do I really sound like that?  That’s horrible, you know?  As I got more used to hearing my style and just hearing what I was doing, I became not so shy, and I started playing in front of my friends and so on.  It kind of went from there.  I did a song in a surf video and that whole community embraced me and told me that I should go for it.

You were also a competitive surfer.  Were you doing your music at the same time?  How do you make the switch from surfing to singing?

I didn’t really ever compete in surfing…

Oh, I’m sorry; I thought I read that you had…

In high school I was on the surf team.  I used to compete in high school, but it was never anything outside of that.  That keeps coming up; it comes up every now and then.  But, you know, around the time that I was surfing in high school and really into surfing, it was kind of the pick up, put down area I was in music.  Because when I was really into surfing, that was all I was doing.  Actually I do recall, we would have all the surf team would get together – because all the surf team, all the guys and the girls, we all just hung out with each other.  So we would go to someone’s house on Friday night and we would play music there, but nobody was really that good.  (laughs) 

Tristan Prettyman

Tristan Prettyman

What’s a bigger thrill – a really great wave or a really good audience?

Umm, oh man.  I’m going to go with the big wave.  I don’t know.  That’s a tough question.

Your Love EP was independently released.  How did you get involved with working with G. Love?

Maybe two years ago I got a call to open up for one of their tours.  I don’t even know… they can’t even remember how they got the CD, but I think it might have been Jack Johnson [who had] given them the CD.  They were looking for someone that was acoustic – one person, one guitar – to go out.  So I got this call to go out and open for them.  We all just became friends.  At that point I had a manager that was just helping me — that wasn’t really a manager, but just my friend — for the beginning.  I was kind of looking to step it up a little bit.  I ended up really hitting it off with G. Love’s manager — his name is Jason — so he became my manager.  I was kind of initiated into the camp.  We did a lot of tours together and whenever they had a couple of shows here and there and needed an opener, I would fly out to wherever and open the shows.  So when it came time to make the record, he just happened to be in LA, and he was like, “I’d love to put some harmonica on something.”  So it just kinda happened.

I’ve read that after Love, you were worried about signing with a major label.  How did you end up signing with Virgin for twentythree and why did you feel they were the right fit for you?

That’s a good question.  In the beginning, because I kind of fell into music as an accident, I wasn’t really too concerned with… I didn’t really have a goal or a point where I want to make it to here, you know?  It was just kind of like whatever was happening was happening.  I wasn’t really too concerned with signing a deal or a label or anything like that.  I was doing the independent.  We were doing really well, so I was just happy with that.  But, the labels started coming around and there was a good bunch of them.  I had a showcase in New York and every label showed up.  I just wasn’t meeting anybody that was sparking any interest.  No real reason… it was kind of like, I’m doing so well on my own, why am I going to sign with you?  Just because it’s the cool thing to do?  I just didn’t find anything that I liked.  But then I met the A&R manager, Josh, from Virgin.  We just hit it off, you know?  Just the way he talked to me and everything was different than everything I had experienced.  He wasn’t so much kissing my ass and like, “We’re really into your music.”  It just didn’t feel fake.  It took a good couple of meetings, and I think one of the most important things to me was I can remember having a meeting with them and I sat down and I was like, so what can you guys do for me?  They were completely shocked.  They were like, “Wow, that’s usually what we ask the artists, but all right.”  It was really kind of cool and I just really hit it off with them.  I played a couple of times at their offices and really dug their staff.  It just felt right.  A lot of the decisions I’ve made have just been on gut feelings.  If something doesn’t feel right, I won’t do it.  It just felt good and I figured, you know, I’ve made it this far and I really haven’t tried to do anything.  I might as well just go for it and see what happens.  If it feels good, and if it doesn’t I can always move on to something else.  It ended up being really, really good though.  It was cool.  And one of the things I was most impressed with was they were more concerned with developing me as an artist over time than like; “We’re going to make this amazing thing and then throw it out there.”   It wasn’t so rushed…

Tristan Prettyman

Tristan Prettyman

“Love, Love, Love” is not only about romantic relationships, but it’s also about being home and having your friends and family around you.  Now that you have an album out and are running around doing tours and press and stuff, does the make it even more special to you?  

Oh yeah, for sure.  I was really excited, because that was the song I wanted to be the single and I was really happy that everyone else agreed.  It’s the song that I really love playing.  It just brings me back to that place where I was when I was writing just for myself.  It’s nice to know that I can always go there.  And I have to go there a lot, which is cool.

“Song for the Rich” was one of the darkest songs on the album.  What inspired you to write the song?  Was there someone specific you knew who was so seriously involved with drugs?

Yeah, it is.  I had a friend who I used to go to church with.  He was the guy that all the girls had a crush on.  He was like untouchable, you know?  But we became friends and we started going to church and we got to know each other really well.  We just became really, really good friends.  Then he started dabbling in drugs and going down the wrong path and getting a little bit distracted.  There were so many of us that were worried about him and he had no idea.   So, the song just wrote itself, and then one night we were all over at his house.  I played it for him and he literally broke down crying.  He just realized… it was one of those moments where you’re like: What are you doing with your life?  It’s not like telling that person is going to change them or make them be like, “Oh, yeah, what am I doing?” and stop instantly.  But, it was a reality check for him.  Especially how I finished the song, in the end of the song it says “watch this song break you down.”  It was really crazy.  I couldn’t play it for a long time, because he used to come to a lot of my shows and he was probably embarrassed by it and knew that a lot of people knew it was about him.  But, he’s doing much better now and I wanted to put it on the record because it was an older song that I used to play a lot and it touched a lot of people.  I used to get a lot of emails or people coming up to me who could really relate to the song, whether it be their parents or their boyfriend or whatever.  I thought… I have no idea how my record got so happy. (laughs)   I’m so used to writing very dark and kind of like sad-hopeful songs and this record turned out so happy.

That was one thing I noticed.  In the album, when the songs turn to love, the songs seemed to be divided mostly the happier relationship songs like “Breathe,” “Always Feel This Way” and “Shy That Way.”  But I also noticed some of the time the relationships are in trouble or dying like in “The Story” or “Electric.”  It’s kind of different, most love songs you hear, in general, tend to be sad songs.  As a songwriter, are you hitting a point where you find happy relationships more interesting than troubled ones or is that just where you are in your life?

Honestly, I have no idea how it happened.  For so long, I had so many people saying, “When are you going to write a happy song?”  I was like, I don’t want to write a happy song, leave me alone!  (laughs)  Everybody loves that sad song they can put on [during] that long drive and listen to it.  I think what happened was when we got in the studio, really if you take all the songs and strip them down, they generally are more like “The Story” and “Electric” and whatnot.  But when you add the accompaniment and I think just the band and I think because all of us got along so well in the studio and had so much fun that that kind of reflected on how the songs turned out.  It’s like the songs were already written, but then we put them in a new environment and it totally… they turned into something else.  I was quite happy with it.  That’s why I put “Song for the Rich” on there, just to kind of balance it out to let people know that it’s not all sunshine all of the time.  The record’s got to reflect my reality and reality in general.

How about Jesse Harris and Lee Alexander, both of whom have worked with Norah Jones?  How did you end up working with them?

Well the label wanted me to do a little bit of co-writing in the very beginning, to just see how I got along.  I’ve never been a big fan of that at all.  If you’re a true singer songwriter, you should be able to write your own stuff.  Have enough to say and that sort of thing…  So I was always against it, kind of offended by it.  (laughs)  I was like, okay, I’ll co-write if you guys let me pick the people I’d like to [work] with.  I love that first Norah Jones record.  I know that Jesse did a lot of the writing on it.  I just love the simplicity of it.  Naturally, he was one person I put on my list.  I had put a lot of people on my list that I knew there would never be any chance of them coming, so then I could get out of co-writing.  (laughs again)  But Jesse listened to the first record and he was like, “cool, I’ll come in and see what happens.”  It was so funny, we sat down and I was like, so have you ever done any co-writing?   He’s like, “No, not really, have you?”  and I’m like no, I don’t really like it.  And he’s like, “Yeah, me neither.”  So we just ended up playing guitar for four hours.  It was awesome.  We just talked and we’re really good friends now.

Tristan Prettyman and Jason Mraz

Tristan Prettyman and Jason Mraz

I loved “Shy That Way,” the duet you did with Jason Mraz.  Since you and he have a personal relationship, did that make it easier or harder to work with him?   

Well, we wrote that song about three years ago.  Which is crazy, because, we wrote it in Vancouver…  Actually, we were just in Vancouver and we played it and it was so weird to be like, wow, we wrote that song three years ago?  That was a long time ago.  When we wrote that song we had only known each other for not even a year.  We were so shy around each other.  I think from the moment we met we were attracted to each other, but neither of us knew what to do about it.  He had just released his record (Ed. note: the 2002 disk Waiting for My Rocket to Come, which included the hits “The Remedy [I Won’t Worry]” and “You & I Both”) and was on a crazy tour.  I was trying to figure out what the hell I was doing with my life.  So we couldn’t really speak to each other.  And then we wrote that song.  We found songwriting as a medium.  We were like, okay, we don’t really talk, I don’t really know you, but let’s write a song together.  (laughs)  Get it out that way.  I think recording it was a little more difficult, now, because we’re dating now, so it was like, well, we’re not really shy anymore…  It became this sort of joke.  That came together very spontaneously.  Most of the duets… me and G. Love did a duet as well and that came about very spontaneously.  Just got bored on the bus one night, so…  That’s how I prefer those kinds of songs to come together.

I love the cover of Britney Spears’ “Toxic” you do on in concert and have on your site.  What made you choose that song?

Yeah, it was my brother’s idea.  My brother lives up in Santa Cruz, so he comes home occasionally.  We were talking about cover songs, and I’ve always been really picky about the songs I cover.  He was like, “God, you should cover ‘Toxic,’ you’d be amazing.”  I just looked at him like he was crazy.  But then I looked into it and I realized it’s a really easy song to play and it’s not actually so bad.  (laughs)  I thought it would be fun to play something and see if people recognized it, you know?  I think the day I learned it I actually had a show and I played it that night.  I was playing with Gary Jules.  I was playing it at soundcheck and he was just loving it.  He was like, “I love this song.  This song sucks so bad, but everybody knows the words to it.”  It gets played so much, it was around so much when it was popular that you just know it – whether you want to know it or not.  It kind of became this thing.  At every show, someone will be yelling out “Play ‘Toxic’!”

Nowadays musicians have so many more ways to reach out to their fans, like your journals on the official site, and your MySpace page.  What is it like being able to communicate with the fans like that?

I love it.  You’re asking if I… (laughs) I’m sorry, I’m so spacing out…

That Robitussin can do that to you sometimes…

I had a radio this morning and I was like, what are the words to this song?  You’re asking about the fan relationship?  I love it.  It’s definitely different for every artist, but for me I’m so honest in my songwriting and I’m such a people person and I have to do it because I was so unpopular as a kid.  I want to be popular, the girl that is friends with everybody.  Because in high school you have the popular girls and they don’t talk to anybody.  So I was like, if I want to be popular and people are going to look up to me, then I want to be as friendly as I can.  Just because I’m like that normally.  It’s cool, I’ve found with the journal entry and keeping it updated, I give a chance for those fans that have been around since the very, very beginning to really kind of grow with me, you know?  And people who are just finding out about the music.  The journals have over time I think become even more honest and more straight talking.

I read the last journal entry on your web site about how you hate interviews that all ask the same things.  I do know what you mean; sometimes we do fall into stock questions.  So I promise I won’t ask the most memorable moment question, which I never would have, or the favorite bands question, which I might have but just for background…  But just curious, looking at it from the other side, if you were a journalist, what do you think you’d want to know about yourself?

I wouldn’t even know, because I know myself too well.  And I don’t even know myself at all sometimes.  That’s the thing, there’s two sides of everything.  I can imagine for a journalist, you have to do your job, too.  But sometimes journalists interview people that they don’t even… it’s just like a work thing, you know?  There’s so many different things for it.

Tristan Prettyman

Tristan Prettyman

Oh sure, I know.  I recently interviewed a singer who released her debut album and we were talking about the songs and she said, “My God, I can’t believe you actually listened to the album.  I’ve been doing so many interviews where they had no idea what the songs were about…”  I thought that was amazing, I couldn’t imagine doing that…

(laughs)  Yeah, definitely.  I did an interview with [a journalist from] Australia this one time.  This girl called, she was like, “So, I guess you just had an album come out?  I don’t know, I think that’s what my boss told me and I’m supposed to be interviewing you.”  And I just felt like, can I just… oh, the line got dropped, sorry…  I don’t want to talk to you if you don’t want to talk to me.

It’s funny, I’ve written a couple books, so a few times I’ve been on the other side, too, so I know how uncomfortable it can be on both sides.

Yeah, but it’s important to me to…  I don’t want to be like, everything’s amazing!  I love my label!  I love doing interviews!  I’m human.  I don’t want to just candy coat everything because I’m supposed to.  And there’ll be times when I complain about touring or whatever to my friends and I had my one friend – she’s so funny – and she’s like, “You don’t appreciate any of this at all.”  No, no, I do, but you just don’t even understand.   And she’s like, “If I were doing it I’d be giving it my all and doing my best.”  I’m trying to give people both sides of it, I guess.  It’s really just how I feel in the moment, which can be completely different than tomorrow.  After I wrote that thing about the interviews, it was almost that I needed to get it out of my system, so that I could get over not being into it and then get back into it.

I also read where in the entry what you wrote about so many people your age feel like they have to follow the pattern; go to college, get a job, move out, find a boyfriend, get married, have children…  You were talking about your parents and how you have found out that they were totally different people than you had always thought as you have gotten older.  Where do you think or hope you’ll be in life when you’re ready to record your album fortythree?

(Laughs)  That’s awesome.  Where do I think I’m going to be at?  You know, some days I would like to think that in ten years I won’t even be playing music and I’ll have another career.  It all just depends.  I think each day you’re getting closer to where you’re supposed to be.  I’m so thankful that I have some of the coolest parents in the world, because they’ve really taught me a lot.  I’ve learned a lot about how they’ve raised me and my brother.  But I’d just like to be happy in life.  And just have a better understanding of myself than I do now, I guess.

In “Smoke,” you ask “Shouldn’t it be that easy to just be happy?”  So, what makes you happy?

Surfing.  (laughs)  Surfing and… I think a lot of girls can relate to this, we’re always after – well, probably not every girl, but – girls are generally after finding the boyfriend and getting the boyfriend and being in a relationship.  For me, now that I’ve found that, I’ve really been able to focus on… it’s like, okay, that’s out of the way, that’s not the thing that’s always on my mind.  Like, yes, I have a boyfriend and I have someone to hang out with and that’s really enabled me to focus on other things, like traveling and the environment and learning about the world around me.  That sort of thing makes me happy.  I feel like I’m a little bit more focused now.  I definitely like being happy with where I’m at in music and being able to tour.  Things are doing well with the album.  That sort of thing makes me happy.  I feel organized.  I feel I’m in the right direction, you know?  And of course, getting to come home and surfing and hanging out with my parents and my friends.  Knowing that when I go home, it feels the same as it always did.  That definitely makes me happy.

Tristan Prettyman

Tristan Prettyman

Almost every article I read about you mentions Jack Johnson as a comparison.  You mentioned you know him earlier.  Other than the fact that you’re both surfers and play acoustic guitar music, I don’t really see that much similarity.  Does it bother you that so many people make the connection?

Yeah, it gets annoying.  But I can’t blame people.  Because I think humans in general, we want to categorize everything.  When something new comes along, we want to be able to identify with it.  And say it’s like this!  Or it’s like that!  Really it’s funny, because Jack is a friend of mine, and I’m just waiting for the call.  Like, you know, “we need to find you another person to compare you to.”  (laughs)  It’s just hilarious.  I crack up because my God, we both surf and we both play the guitar, but I don’t think our music is anything alike.  I don’t consider my music happy surf music or anything, you know?  Sometimes I wish that it was.  I love that kind of music.  The thing, though, for me is that’s why I look forward to making a lot of other albums.  I wanted this album to be the first step.  I want to get better with every album.  I want some people not to get it at first, so that it’s this thing that you get over time.  Like over three albums and four albums you’ll really get a sense of who I am as an artist.  I’m so young and I’m still trying to find my style.  I’m still developing.  I want it to be something that withstands time, so that I can identify… just be myself.  Not be like everybody else.

Radio playlists are so regimented these days.  Years ago, you used to be able to hear rock, pop, country, folk and soul on the same station and that just doesn’t happen anymore.  Do you think that can make it tougher for a band to find an audience?

Oh, definitely.  I’ve seen it on the road.  Like James Blunt is on the road with us.  I play and he plays and then Jason plays.  Definitely he’s getting more play than me…

Yeah, I’ve been hearing “You’re Beautiful” all over the place…

And he’s getting more play than Jason.  We just had a couple of shows where he flew back to England and everyone’s asking where he is.  It’s just amazing.  He is getting so much radio play and the video is getting played.  That reaches so many more people.  When you hear something on the radio, like four or five times a day, whether you like it or not, just because you’re hearing it so much you’re going to like it, you’re going to recognize it.  We did a fair amount of radio play with “Love, Love, Love” and the stations that picked it up really supported it.  It was either stations picked it up or they didn’t.  Unfortunately, there were more stations that didn’t pick it up…  But it’s the reason that I tour.  Because who knows if that person that gets so much radio play is going to be able to have a second single or where are they going to be after that.  I feel like, I love touring.  Touring is a way for people to hear your music.  They’re kind of discovering it.  I think you get more of a real fan base that way.  I think that if you tour a whole bunch you can definitely acquire a large audience by word of mouth.  It’s more fun, because you’re giving people a taste of everything you do.  Not just people know you by just one song.

One last question and it’s more serious.  On your website you have a very prominently placed link for donations for relief for Hurricane Katrina.  Obviously, everyone has been greatly moved by the tragedy, but tell me how the disaster affected you and what moved you to do what you could to help?

Well, for me I had a lot of people, a lot of fans actually writing to me that were in it.  When you’re traveling… I think with all the disasters that have happened in the last few years, from 9/11 to the tsunami to those hurricanes that came through… and living in California we’re so far removed from any of the disasters that have happened lately.  I feel like a lot of people that weren’t right in it, you don’t realize how gnarled it is, you know?  It only takes – you know if everybody in the world donated a dollar, that’s a lot of money that would help.  I think this is important for everybody to raise awareness.  Certainly I have a lot of people who visit my website, so I figured, I don’t get a ton of traffic, but at least it’s up there and it’s only a click away, you know?  I think it’s just important.  That’s what living in this country is about, supporting each other and having some kind of freedom.  Just helping each other, you know?  I certainly donated a good chunk of money.

Copyright ©2005 All rights reserved. Posted: November 25, 2005.

Photo Credits:#1 © 2005.  Courtesy of Virgin Records.  All rights reserved.#2 © 2005.  Courtesy of Virgin Records.  All rights reserved.#3 © 2005.  Courtesy of Virgin Records.  All rights reserved.#4 © 2005.  Courtesy of Virgin Records.  All rights reserved.#5 © 2005.  Courtesy of Virgin Records.  All rights reserved.#6 © 2005.  Courtesy of Virgin Records.  All rights reserved.

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