Ricky Montgomery is growing up from “pop boy sh*t” with his deluxe album Rick(y). Released on May 10, the album is a continuation of his 2023 sophomore album, Rick an exploration of grief and stories from Montgomery’s adolescence. For Montgomery’s Rick(y), the indie pop artist sat down with EnVi over Zoom to talk about growing up artistically, musical influences, and more.

Nostalgia’s Necessity

Before Rick and Rick(y), the last full album Montgomery put out was in 2016 with Montgomery Ricky. That album was full of sleeper hits released without major label support and later found traction on TikTok. Now, Montgomery is signed with Warner Records. This development led him to release both versions of his second album. Montgomery said that with the new step in his career and Rick(y), he needed to look back first.

“Having a long pause between the two albums, like, kind of made it so I had to, like, make a nostalgic album,” Montgomery explained. He’s “reflecting on things” he “talked about as a teenager on songs with a bit more awareness.” With Rick, it was a chance to say goodbye to his previous works. “I wanted to make something that was a little bit more about vulnerability and about making and just having adult experiences.” 

With the deluxe album’s release, Montgomery’s moving on and closing a chapter. “I’m trying to say goodbye to old, kind of trauma dumpy things on Rick and get it all out at once so I can move on to just kind of making music afterward,” he said. 

Inspiration Across Genres

There were multiple albums and artists that influenced Montgomery’s growth as an artist, especially with the storytelling on Rick and Rick(y). With the recent album, Kendrick Lamar’s Mr. Morale & The Big Steppersand Mount Erie’s A Crow Looked at Me both pushed him toward that vulnerability. Kendrick Lamar’s album was about “the internal stuff” and Mount Erie’s was a “poetic” and “collage type of record.” These aspects helped shape the story of Rick and Rick(y).

A more evident influence on Rick(y) is the presence of a cover of “Reptilia” by The Strokes, though its presence on the album is purely because of opportunity. The cover, which had been sitting on the shelf from another project, was still unreleased, and Montgomery wanted it out. “Eventually I just said, ‘You know what, let’s just put this out ourselves. I like it. Why not?’”

The spirit of The Strokes is present through their original song, but Montgomery made an effort to make it his own. Over two days of recording, he made two versions of “Reptilia,” one more in line with the original’s style, and one more his own. “I wanted to do a much more, kind of, true-to-myself version and a different sounding version,” Montgomery said.

Making Meaning

Montgomery explained his approach to music is similar to a Rorschach test after mentioning it in a TikTok video. “I don’t know that all art is better as a Rorschach test. I think some stuff can be really cool when it’s direct and very plain spoken,” he expressed. For his own music, it’s a bit different though. The “wave” he’s on right now is based more in ambiguity and allowing listeners to find their own meanings in his music.

One song on the deluxe album that falls into this category is “It’s Ok to Cry.” Just listening to the song, the lyrics tell a story of loss and accepting that “it’s ok” to express the emotions that come with it. The story of the song, however, is pulled straight from Montgomery’s life experiences. He was quarantined away from his family in 2021 when his family dog, Lily, passed away. After her death, writing a song about this experience came to him naturally. However, he still wanted it to be broadly applicable for people, all while not taking away what it meant for him. “I think once you recontextualize them [ lyrics and chorus] as a song about saying goodbye to your pet, they make a lot more sense and the song broadly does too,” he said.

Montgomery said he’s evolved in balancing directness and openness. Compared to his earlier pop-punk inspirations like Green Day, which tended to be more direct in their lyricism, he’s grown to be a bit more abstract. He likes to “toe the line” between what he simplified as “dumb” and “smart” ways of listening to music. He clarified it’s not a difference in intelligence, just applicability and relatability. “It’s good to have that healthy balance of, you know, like ‘Oh, here’s something, like, broadly applicable everyone understands,’ but also … it’s nice to have depth too.”

“I want to stay a little dumb,” he asserted, “so I can participate in culture broadly.” He’s thankful that at 31 years old he still feels “pretty dumb as a music listener, and that’s a good thing.” One thing he’s noticed though, is that fans “don’t participate in the same parts of music culture as I do,” he suggested, but noted that they often align when it comes to people he personally knows.

It’s Time to “Settle Down”

Every part of life is a mixture of happiness and dread, but the joy of having released these albums isn’t lost on Montgomery. “I’m so happy to have two albums done. I had one album done for so many years, and now I have two. And with this next deluxe album, you could even argue there’s like, two and a half!”

Having his music out for both himself and fans isn’t just fulfilling, it’s freeing for the singer too. “Having so much music out,” Montgomery said, will give him “a little bit more ability to reengage with music in a more excited way and not feel the pressure of a second album.”

Without the pressure that came with his move to a major label post-TikTok blow up in 2020, “Now I can kind of just enjoy,” he said. Not only is he enjoying the new environment around him, but is also able to settle down a bit too. “I’m excited to begin what feels like the first album in like, my proper, like, artist career phase.” With the release of Rick(y), he’s moving into the next era.

“Now, I can finally take my time, enjoy my life, and hopefully make music that reflects those feelings.” 

Image courtesy of Mal Peterson

Keep up with Ricky Montgomery’s music and tour on Instagram, X, and TikTok. Stream Rick(y) on Spotify, Apple Music, and other platforms.

Looking for more indie artists? Check out EnVi’s interview with Mona Vera!