Ryan Montgomery

Ryan Montgomery, a native of Lake Worth, Florida, has been making waves in the country music scene since his breakout in 2017, when he started performing covers from the back of his tailgate at his local amphitheater in South Florida. At age 18, Montgomery recorded his first 6-song EP in Nashville and 1-year later played the main stage with Morgan Wallen, Riley Green, Chase Rice, Chris Lane and Kip Moore, at that same amphitheater. 

Since, Montgomery has independently released an additional 5 EP’s totaling 27 songs recording in Nashville with top industry professionals.  Today, Montgomery has over 10 million combined streams, multiple top 10 iTunes chart placements, over 500,000 social media followers, and is selling out headlining shows across the country at venues with capacities ranging from 1000 to 5000.

Montgomery’s most recent smash hit, “Sun, Sand, Drink in My Hand,” released June 6, 2025, is his most authentic track yet—a windows-down anthem that captures the spirit of his coastal roots. Born and raised on Florida’s east coast, Ryan still finds his escape barefoot in the sand or out on the boat, and this song channels that lifestyle with every beat. It’s a celebration of slowing down, soaking up the sun, and living in the moment—something Ryan knows firsthand.

The official music video brings that feeling to life, shot on the beaches of his home state and filled with scenes that reflect the real way he unwinds when he’s not on the road or in the studio. With “Sun, Sand, Drink in My Hand,” Ryan invites fans to join him in the place where he feels most himself—and reminds us all to take a break and breathe in the good stuff.

Early Life

Although music was always a special part of Ryan’s life, he had other interests as a youth as well.  Growing up in South Florida allowed Ryan to participate in numerous sports and his athleticism enabled him to excel in many including travel ice hockey, basketball, competitive waterskiing, surfing and working out.  Ryan was able to successfully balance school, sports and music throughout his elementary, middle and high school years and as he entered college made a decision to focus primarily on music.  

Career

Montgomery was just out of high school when he decided to park his truck in the middle of thousands of country music fans and perform right off the back of his tailgate for the crowd tailgating outside the Coral Sky Amphitheater in his hometown of Lake Worth, Florida.  Little did he know at the time, that he would be performing on the main stage and in the lineup with Morgan Wallen, Riley Green, Chase Rice, Chris Lane and Kip Moore at one of South Florida’s largest country music festivals inside that very same amphitheater just 2 short years later. 

Montgomery released his debut single “Drop a Tailgate” June 3rd, 2018 (#116 iTunes Country Chart) and self-titled 6-song debut EP June 29th (top 15 iTunes Country Chart, top 100 iTunes All Genres Chart). 

On January 4, 2020 he released his sophomore EP and single, “Buzzed at First Sight” which included the September 6, 2019 single release of “Til the Sun Came Up” and the May 10, 2019 single release of “Buy You A Drink” (#37 iTunes Country Chart). 

Montgomery's third EP, "We Brought the Party",  recently released on January 8th, 2021 (#6 iTunes Chart and #15 All Charts) features "Mexico Memories, "Windows Down", "Summertime Teenage Dream" and "We Brought the Party".

On January 7, 2022 , Montgomery released his brand new 5-song EP, “Chasing Sunsets” (ranked #4 on iTunes Country Charts  sitting right behind country music icon Jason Aldean). Produced by Montgomery, "Chasing Sunsets" features two brand new singles, ‘"Chasing Sunsets” and “Waiting on a Friday Night” plus three previously released singles, “Nashville and Hawaii” (released March 26,2021) and “These are the Days” and “Sundown Saturday Night” (released June 4, 2021).

On October 25, 2024 Montgomery released his highly anticipated 7-song EP, Lettin' the Night Roll, which features "All Summer Long," "Whiskey & Smoke," "Missin' a Girl," "Ride Around," “Lettin' the Night Roll” and 2 acoustic bonus tracks of "Whiskey & Smoke" and “Missin' a Girl,” offering a deep dive into his latest work. These songs are a collaboration with Sony Publishing, Peer Music Group and hitmakers Ashley Gorley, Jaren Johnston, Jordan Schmidt, Justin Ebach, Chris DeStefano, Jaron Boyer, Michael Tyler and Josh Phillips, the masterminds behind #1 hits from Florida Georgia Line, Jason Aldean, Luke Bryan, Kenny Chesney, Tim McGraw, Morgan Wallen, Luke Combs, and countless others. Co-produced with Brandon Hood, whose impressive track record includes recordings by country heavyweights such as Rascal Flatts and Sam Hunt, and mixed by Grammy Award winning F. Reid Shippen, “Lettin' the Night Roll” is a true reflection of Ryan’s artistry showcasing his authentic rock / hip hop / traditional infused sound with a distinct  storytelling and lyrical style.

Montgomery has written and produced 24 of his 27 released songs and at age 26 has officially released 5 EP's featuring 27 songs as an independent artist, recording with Nashville's top session players and engineers including David Huff, F. Reid Shippen, multiple GRAMMY award-winning mixer, engineer, and producer, and Pete Lyman, GRAMMY-nominated mastering engineer. 

Montgomery has a combined social media following of 500K+ with fans packing his shows and downloading/streaming his music. Besides writing and recording new music, Ryan loves performing and has been selling out shows on his headlining tours taking him through Fl, GA, NC, SC, AL, MS, LA, TX, TN, OH and IL and other U.S. locations.