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Ricky Montgomery on "Montgomery Ricky," artistic reinvention and the double-edged sword of social media stardom

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As the most beautifully executed April Fools prank of 2016, Ricky Montgomery released his long-awaited first LP, “Montgomery Ricky,” on March 31st a few minutes before midnight. The album, for which fans have been crossing their fingers since last summer, is a carefully crafted, innovative work of alt-pop that was well worth the wait. “Montgomery Ricky” takes the genre of pop, flips it upside down and kicks it around a little. It recalls the sounds of peak-artistry albums like Vampire Weekend’s “Modern Vampires of the City,” Panic! at the Disco’s underrated “Pretty. Odd.” and somehow also The Killers’ “Sam’s Town.” It’s fun, angsty, emotionally intelligent, genuine and catchy as hell. The album isn’t built for any one mood but instead moves deftly between snarky, danceable tracks like “California” and earnest, sober ballads like “Mr Loverman.” It’s a first major release that shows Montgomery has been working at this much longer than his discography would suggest, and predicts a promising future trajectory, especially given his dedication to constant reinvention, which he described in an interview with Up to Tempo. “I really resonate with the practice of rebuilding — tearing it down and always forcing yourself to get better. Not only at what you’ve done, but as an artist starting over and letting things die because they’re over and they don’t need to go on,” Montgomery said. “I think that’s just a sign of true artistry — continually reinventing yourself and reinventing the way that you express yourself. That’s the way that you arrived at your earlier art, so why would you sacrifice that practice to recreate something you’ve already done?” “Montgomery Ricky” is full of angst, longing (romantic and otherwise), and a bit of anger at times. The album, in some ways, acted as a space for Montgomery to work out grief and struggles with personal flaws. “It’s about self-acceptance. It’s about looking at yourself objectively and admitting to yourself the things that are holding you back and the things that need to change, but also the things that are good about you right now. … Specifically for me, I’ve had a lot of problems with co-dependency, which a lot of people struggle with, in regard to relationships not only with romantic partners but with parts of my life that I don’t want to leave behind, like living in L.A.,” he said. “It’s also about battling pride and not letting your own intentions cloud your vision or cause you to put harm on others, emotionally. Also, it’s about dealing with my dad’s death when I was 15. It’s a lot of that. That’s a big sub plot through all of it. I will say, there’s only one love song on the album, actually, and that’s ‘My Heart is Buried in Venice.’” Montgomery is originally from Los Angeles, but he moved to St. Louis with his mother at age 12, and then spent summer and winter vacations back in L.A. with his father until his death at age 15. Moving back to Los Angeles had been a goal ever since Montgomery left the city, and he finally moved back this past summer. “I guess I always felt like I was torn away from the place that I really wanted to be, … and I attached a lot of angst to that. It was always my goal to move back here because it made me feel like I was in control of my life, where I was living it,” Montgomery said. “Now that I’m here I definitely feel like I’ve gotten closure with that part of my life. I see L.A. for what it is now, which is a horribly laid out city with terrible infrastructure. Now that I’ve moved here, I can live anywhere, but I always needed to live here at one point …" Montgomery now works at a bakery during the day but leaves significant time and space in his life for music. “I like having day jobs. I think it keeps people humble. It can be inspiring in its own way, just by seeing how horribly people treat food service people,” Montgomery said. “[But] I don’t overwork myself. … I leave a lot, a lot of time to band rehearsals and to writing and to just focusing on stuff and listening to music. I listen to at least one new album every single day, just out of habit at this point.” With the album’s release come two music videos for the singles, “This December” and “Dont Know How.” While complementary to the tracks, both of the videos also show the comedic talent which has earned Montgomery a dedicated base of over 180,000 followers on Vine and other social media—they are strange, hilarious, and you can’t look away. The video for “This December,” like the lyrics of the song, starts out seemingly innocent but quickly heads down a path of red flags. The choice in sweater was what first captured my interest. But Montgomery is masterful at absolutely-batshit-but-keeping-it-under-wraps eyes. Watch the video below now to avoid unfortunate spoilers.

“My favorite thing about that video is that we’ve got a bunch of ‘easter eggs’ hidden in there. I didn’t want it to be specific to a holiday, because everyone thinks that it’s a Christmas video, but I’ll say that it’s very obvious in that video that the girl is Jewish and you’ll have to figure out why. That’s all I’ll say.” “Dont Know How,” directed by Dylan Schnitker, opens on Montgomery in a dark, misty space looking like some strange sort of Cleopatra, most notably because he is wearing a metal headdress made of dangling spoons. Weird enough to begin with, the video still manages to surprise you and dart off in a hilariously unpredictable direction. Watch below now.

“Originally we had this idea of renting out a warehouse in the middle of downtown St. Louis and getting … people to just congregate and crawl over each other for a while,” Montgomery said. “We wanted to be as weird as we could in sort of the way that Tyler, the Creator was for the video for {“Yonkers.”] We wanted to go for the same sort of vibe, like, it’s so weird you can’t look away. And that’s sort of the same thing we ended up using for the beginning of this video.”
A minute in, Montgomery’s (real life) mom opens the door, revealing that he has actually been filming the video alone in his basement. They argue. For a very long time. Then his entire (real life) family goes to a tennis match. It goes on for multiple minutes and the song finishes. “We wanted to end it, originally, at a volleyball game, because my brother actually plays volleyball, but we ended up going for a tennis game because it was easier to organize,” he said. “The best thing about that video … is that literally no one in the video can play tennis. And it’s specifically shot to hide that. It’s a lot of people just swinging rackets.” Montgomery’s first EP, “Caught on the Moon,” was released in 2014. Met with strong success, he went on to record what would become "Montgomery Ricky" and created a Kickstarter, which he referred to as “The Rickstarter,” to help defray the costs of production. Montgomery offered rewards such as Twitter shoutouts and follows or a personal Skype concert and The Rickstarter met its goal in 30 days. According to Montgomery, the Rickstarter funds covered about half of all the costs involved in making the album. This allowed Montgomery to produce a polished album while still remaining an independent musician. Without a label, a large number of tasks become Montgomery’s own responsibilities, but he highly values the freedom involved in independent production. “… There’s a lot of stuff that falls on me instead of a marketing team or a label or anything else. … You know, just little tedious things that end up taking up much more of your time than you’re anticipating ...” Montgomery said. “It can be stressful, but ultimately I like the control of being an independent musician and I wouldn’t trade it for anything. I have the tendency to micromanage anything that has my brand attached to it, because I care about it. I think a lot of people are that way. … Ultimately, the freedom outweighs the tedious things that come with doing it all yourself.” Jon Heisserer, a former member of the St. Louis alt-rock band Building Rome, has been working as Montgomery’s producer and acted as a strong source of support through the entire recording and production process. “He’s been part of the music industry for ten years and is sort of a guiding hand through a lot of stuff. I’m very, very thankful that I’ve got someone like him to help me not go into things completely blindly,” Montgomery said. In late March, Montgomery and his band made their performance debut at Valencia High School. Caleb Hurst, a fellow Viner, plays guitar and sings back-up vocals and Ben Russin, a friend since kindergarten, plays bass. There are hopes of touring nationally soon. “I tried to schedule a tour but it turned out that mainly the tour van was making it impossible, just the expenses. It’s so expensive to go on tour, I never really knew exactly how expensive it was,” Montgomery said. “I do have plans, but as of right now I am a local L.A. artist by necessity.” The band played another show last week at El Cid. Montgomery has been playing in bands around St. Louis since he was 14, but really got his start on Vine. Part of his Vine content is really great dry humor and part of it is music – sometimes quick covers, but mostly 6-second original clips that are as yet unattached to a full song. They’re typically really lovely – like this beauty– and often they’re really funny – like my fave here. Above all, Montgomery maintains an admirable level of self-awareness about his internet presence. “It can be sort of an eye roll-y statement to talk about your brand, but it’s something you at least have to do quietly by yourself to yourself – talk about what exactly you’re trying to put off and how you want it to be interpreted and what you want to keep to yourself and not divulge in the process of making it,” Montgomery said. “I do realize how tacky it can be, but ultimately you just have to swallow your pride and admit to what you’re doing, because everyone has a brand who’s doing internet anything – anyone who’s doing anything has a brand. And I’m all about just being blunt about that kind of stuff and not trying to front. I don’t want to trick people. I like to be honest about what I’m doing. Hopefully that plays through.” Montgomery’s internet following has influenced his music career both directly and indirectly. Two years ago, Montgomery was attending school at University of Missouri when he was offered an internship at Adult Swim in New York based off of his comedic success on Vine. He finished the semester but ultimately dropped out to pursue the internship and other creative interests. He has never looked back. “It got me into the world and I would not have done that if I hadn’t done Vine. I would have still been in college in the middle of Missouri trying to be a journalist or something. It gave me the courage to pursue what I really wanted to pursue. That was really important for me,” Montgomery said. “Since then, I’ve … made a point to only pursue the things that deep down I really want to pursue, and if it doesn’t feel right I won’t do it ... It’s given me a voice, but also a way to be the person that I’ve always wanted to be, and to be honest with myself, to have this sense of peace I wouldn’t have had otherwise. Not because of the popularity, but because of the ability to pursue my actual aspirations.” Success and followers on Vine have clearly contributed to success in Montgomery’s music career, but there is a compelling struggle in the juxtaposition between his dry style of humor and his emotionally genuine music. “There’s a lot of cognitive dissonance there, and it did affect my Vine output, actually, when I was making the album because … in my internet persona I am very removed on purpose, and when you make music you can’t really do that in the same way. I had to do both things which drove me insane for a while. It’s not healthy. But I guess they’re just different sides of who I am,” Montgomery said. “They do converge sometimes. I’ll have a line that’s supposed to be funny in a song or light-hearted amid all these dark things, … like the second verse in ‘This December’ when I talk very blatantly about murder. I guess I’ve always liked that – I’ve always liked mixing personalities and creating a more dynamic picture. That’s something that I want to do more of – mixing things and keeping people guessing what’s coming next. I don’t want to be predictable. That’s … part of where the brand comes from and where it’s going.” Montgomery also spoke to the two sides of internet popularity: affirmation and the fear of stagnation. “It’s a lot of things. It’s obviously rewarding to see those numbers go up, … but it’s also stressful when they don’t go up as much as they do other times. You end up kind of depressed, like, ‘What am I doing?’ You don’t feel funny anymore. It’s this vicious cycle of always wanting to grow, [but] inevitably you’re going to plateau at some point, so there’s a lot of stress attached to that as well, the impending plateau,” Montgomery said. “I don’t know if it’s a good or bad thing. It’s good because, you know, a lot of people make a lot of money off of it and it’s fun to watch and it’s fun to do, but it’s also stressful because it can turn a lot of people into shells of themselves, just trying to make money and appeal to what they believe is the latest trend or thing that kids are into, and they never really put themselves into it. I resent that about it, which isn’t the fault of anyone but the people making the content. It’s a mixed bag.” He sees it as unescapable that eventually one’s growing popularity and acclaim will slow, hopefully with a solid fan base still intact, and that can either be motivating or comforting. “I think that’s just the nature of being popular, at some point you reach an apex. We can’t all be Kayne West, we can’t all continually grow. If you do, then inevitably you’re going to be really polarizing and just become a parody of yourself, so I think that a plateau is inevitable and also healthy for a lot of reasons," Montgomery said. “But it’s not to say [any plateau is] going to last forever. There are re-plateaus and it’s up to you to take that further.” Ultimately, Montgomery plans to continue growing and taking his music to new places, and hopes to become a musician first in people’s minds, not a Viner who also makes music. “I’ve been writing another album for a while. I’m trying to reinvent myself and become better and make a much better album, which I will do,” Montgomery said. “Hopefully just playing more shows and becoming more of a musician and less of a Viner. That’s sort of been the dream for a while, separating the two. … I just want to be able to do music and not have to tell anybody about it while I’m doing it so I can just focus on it and not make it an interactive experience … I’m naturally a very isolated person, very introverted, and it contradicts that to always tell people about what I’m doing.”

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