The Forum

A former student of St Louis Community College is proving that success isn’t always entirely within the bounds of a traditional academic path and that community college can be a powerful tool for aspiring creators.  

You may know Montgomery for his debut album “Montgomery Ricky,” a powerful album released in 2016 and really ramping up in popularity during 2020 when his songs “Line Without a Hook” and “Mr. Loverman” went viral on Tiktok. It may surprise you however to learn that Platinum musician began some of his first performances on the stages of St Louis.

Montgomery’s journey to success began through a mix of early exposure and creativity. Spurred by a bout of spite, Montgomery taught himself the guitar after being told doing so would be “too hard”. “And I said, ‘Oh yeah, too hard? Okay, watch me.’ And then I taught myself guitar. And now I’m being interviewed as a successful musician from the school. There you go. That shows him—so frankly, eat my shorts.”  

Montgomery felt he had started guitar “too late” and his high school guitar classes offered little beyond the basics. “—there was beginner guitar and advanced guitar, which really should have been called beginner guitar too, ‘cause there was nothing advanced about it.“ 

But sure enough Montgomery would book his first show at a venue in STL known as Fubar at just 14. 

“My first show ever was at Fubar, which I think is back now. It was a new venue when I first booked the show there and then it shut down over COVID and I believe it’s back. I don’t remember, but yeah, Fubar.” 

“So I guess short answer, I got my start on MySpace as like a very bored kid in west St. Louis County.”

But more than music Montgomery reflected on his time in St Louis. At around 16-17 he would get his first (and one of his worst) job(s) at Chesterfield Mall (now closed) working at Auntie Anne’s. From there he would shift to working at B&B Theatres otherwise known as Wildwood 10. He also reflects on his time growing up in South County, Montgomery said he was present during the 2014 Ferguson protests following the killing of Michael Brown. He recalled being there during key demonstrations, including the day of the grand jury decision, describing it as “a tumultuous time”  

Following those years Montgomery began his time at St Louis Community College. He attended from 2011 to 2013 where he pursued a general transfer degree and took advantage of every opportunity available to infinity and farther beyond the classroom walls. He participated in the A+ scholarship program, worked as a student ambassador at the Wildwood campus, and was actively involved in student life through campus events like open mic nights. He also worked in the campus bookstore, an experience he continued even after graduating due to his family connection to the job. 

Montgomery credits STLCC with giving him a more personal and diverse educational environment than larger universities, pointing to small class sizes and the wide age range of students as especially formative. He recalls learning alongside both traditional students and older, continuing education students, which helped him become more comfortable communicating across generations.

Montgomery felt he had started guitar “too late” and his high school guitar classes offered little beyond the basics. “—there was beginner guitar and advanced guitar, which really should have been called beginner guitar too, ‘cause there was nothing advanced about it.“ 

But sure enough Montgomery would book his first show at a venue in STL known as Fubar at just 14.

“I really thought that I got a better educational experience at STLCC ‘cause of the class size… you’re more intimate.” 

“Being there with continuing ed students that were in their fifties… it made me more comfortable around adults.” 

He also took part in a study abroad program in Canterbury, England in 2012, which he attended at the earliest possible point in his college career and noted that he was the youngest student in the program. 

Beyond academics, he describes STLCC as a place where he developed confidence, networking skills, and early professional habits. The campus open mic nights in Wildwood were especially influential, often placing him in informal leadership roles such as emceeing or running sound. 

“I would show up wanting to play a song or two… and by the end of the night they would have me running sound or emceeing.”

Shortly after Montgomery would join the then brand new app Vine, a seed of his early success and unexpectedly shaping the next step in his career.

“In January of 2013 I had gotten my first smartphone. I think I was 19, I never had a smartphone before… I was looking at every app… I just got any app, Apple News, CNN, whatever it was at the time, and I found Vine about the day it launched.” 

Montgomery’s time on Vine eventually expanded beyond online visibility into real-world industry opportunities. After enrolling at the University of Missouri, he found himself frustrated with how few of his credits transferred and disillusioned with the structure of the program. While still navigating college, he was offered a paid internship with Adult Swim through a connection in the early digital creator space.

“None of my credits transferred—and I, you know, I hope that people that are working there now are a little bit more aware of how strict Mizzou is on their pre-reqs.” 

He describes the decision as immediate. In the middle of a lecture, he recalls standing up and leaving class, ultimately choosing to step away from his university path to pursue the opportunity instead. He would later move to New York City for the internship, marking a sharp transition from student life in Missouri to working inside the entertainment industry.

“I was in a lecture hall at Mizzou and I stood up. And I was in the middle of class, and it was like intro to journalism or something and I just looked around and then I just walked to my car and I drove home to St. Louis.”  

Looking back, Montgomery ties much of his trajectory not just to talent, but to how he approached relationships and visibility online. For aspiring artists, he emphasizes consistency over perfection, especially in the digital space.

“You just gotta’ be more regular with your posting… tomorrow never comes. You’re never gonna’ have a good day to sit down and schedule out months’ worth of content.”

He also stresses that momentum matters more than polish, encouraging young creators to prioritize output over overthinking.

“Be less precious about the quality of the videos you post. Just get them up there and focus on momentum and maintaining momentum.”

For Montgomery, the lesson isn’t just about social media—it’s about how creative careers form today: through repetition, visibility, and willingness to act before everything feels fully planned.

If you’d like to listen to the Forum’s interview with Ricky Montgomery, stay tuned! We’ll be posting the interview sometime this month to the Forum’s webpage.