Drey's early career began as a songwriter. She won over eight multiple songwriting awards including the 2004 VH1Songwriting Contest, the Gibson GuitarDallas Songwriting Contest for "Stand in Line" and the grand prize in the 6th Great American Song Contest for her song "Impossibility". This continued onto international competitions including the International Songwriting Competition for "Killin' Me", which eventually became her first radio dance hit. It was soon after that her first radio single "Just Like That" was produced by Nile Rodgers and was adopted as the battle song for the 2004 World Series Champions, the Boston Red Sox. The chorus of the song, revised to "Reverse the Curse, Just Like That", played at the televised home games, reaching an audience of over 12.5 million baseball fans each week. This continued with Song of the Year Contest for a win in two categories for best dance song and pop song. After teaming up with co-writer and producer Kevin Churko, multiple Juno Award-winning producer-writer whose credits include Shania Twain, Ozzy Osbourne, Five Finger Death Punch and more, a number of her songs succeeded on the charts. In 2005, "Killin' Me " rose to number 11 on Billboard's Hot Dance Airplay and number 6 on the Hot Dance Music/Club Play chart. The follow-up, "Why Should I Believe You", peaked in Billboard's Hot Dance Airplay at number 24 and the Hot Dance Music/Club Play Top 10 in 2006. Later that year, Drey was signed to dance record labelRobbins Entertainment and she wrote and performed the dance-pop single "By the Way". It became her most successful single on Billboard's Hot Dance Airplay chart, peaking at number 4, maintaining a chart position for over 10 weeks. On the Hot Dance Club Play chart, it was her third consecutive top-twenty hit, reaching number 19. In fall 2008, her single "All Out Of Love" was played by both Hot AC and Soft AC radio stations across the country. With a review feature from Chuck Taylor at Billboard Magazine, the single found its way across a wide variety of stations in the U.S., including WKTU in New York City and KBIG Los Angeles, as well as making its way to the R&R Top 40 Indicator charts. The founder of Monster Cable, Noel Lee, agreed to use Drey's dance hit "Why Should I Believe You" to film the first music video ever in WMV HD with 7.1 digital audio. It was filmed at Microsoft Studios in Washington, and the content was used in a nationwide, big chain store calibration video called "Monster / ISF HDTV Calibration Wizard DVD", which was also narrated by Drey. In 2008, Drey performed in Beatstock at Jones Beach in NY and the PCN Bank Arts Center with artists such as Basshunter, The Pussycat Dolls, September, and more. In 2011, Drey released "Can't Let Go" which received airplay on reporting dance leaning stations such as C89.5 Seattle, Music Choice, WNRG 107.9 and more which made top 100 most played Dance songs of the Year. In the summer 2012, she released "Summer Night in Seattle". . Drey has had songs appear in TV and film, licensed for such shows as America's Next Top Model, the new DVD re-pressings for shows Beverly Hills 90210 and Melrose Place, and a feature song, "Let's Go Ride It", in the motion picture Bachelor Party Vegas. Her original song "Don't Wanna Cry Anymore" was a feature song in the motion picture '‘The Big Gay Musical’'. Jenna Drey has been the headliner performer in club venues and a particular favorite of Gay Pride events. Drey has been the headliner at some of the biggest Pride events in the U.S., including the Washington, D.C., 2012 Seattle, Chicago, Providence, Houston, Ft. Lauderdale, Phoenix, 2010 Flagstaff, and Minneapolis.
