On April 1, 2016, a new name emerged in the indie music world, quickly developing in tandem with the social media boom. Singer-songwriter Ricky Montgomery‘s inversely self-titled debut album Montgomery Ricky was 35 minutes of sincere, imaginative lyricism and pure boyish bedroom-pop charm, but its trajectory turned out to be a slow burn. It wasn’t until 2020, amidst the global pandemic, that not one, but two songs from the record were swept up in a TikTok storm and became impossibly viral hits.
A decade in, Montgomery Ricky remains the centerpiece of Montgomery’s career; it has aged in a way that other mid-2010s pop records could only hope for. There’s a reason why it took over the internet four years after its release, and why six years after that, crowds of fans still scream-sing every word back. Whether you discovered “Line Without A Hook” in the midst of young heartbreak or “Mr. Loverman” as the soundtrack to anime edits on TikTok, chances are the songs have stuck with you, intertwining themselves with lasting memories. I, like most people, discovered Ricky’s music in 2020, but my first time seeing him live was at a college show he played at my university in early 2024. So for me, his music evokes both lockdown-era melancholy and the fondness of my college years spent going to shows with friends, the days that got me truly and irreparably obsessed with live music.
In honor of the album’s anniversary, Ricky played a trilogy of shows: in his hometowns of Los Angeles and St. Louis, as well as a New York City show in between. There’s no understating the exhilaration that was in sold-out Brooklyn Steel on Saturday night. The crowd laughed at the pre-show playlist that cleverly interjected Ricky’s name into iconic songs – we all know Disturbed’s hard-rock hit “Down With the Rick-ness”… right? They cheered at the mere mention of their favorite anime characters. They showed their love for the opening act, Bella Kay, who recently had her own moment of virality with breakout hit “iloveitiloveitiloveit.”
Ricky Montgomery took the stage, forehead adorned with a painted third eye in reference to his debut album’s cover, and he had not a moment to waste. He played the debut album front to back, not just going through the motions that you might see from artists playing older material, but truly performing. Stepping down from the stage to interact with fans, posing playfully for the photographers’ cameras, Ricky’s engagement with the crowd is unmatched. He even brought a fan on stage to play guitar on “Mr. Loverman,” a tradition he has newly started. He also played “Oh My My,” the recently unearthed predecessor to “Line Without A Hook” that was released with the anniversary edition of Montgomery Ricky, which includes three never-before-heard songs.
Ricky Montgomery has matured a lot, both as a person and a musician, in the years since he wrote his first songs as a teenager. He’s had to contend with the many ups and downs of internet fame and the struggles of trying to make it in the wildly competitive music industry while remaining faithful to the craft. Montgomery Ricky did what a debut album is meant to do: it laid the foundation for his musical identity, his evolution in sophomore album Rick, and everything beyond. This show was an homage not just to where it all began ten years ago, but how far he’s come, how much he’s persevered, and where he will go next.
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