Drey's early career began as a songwriter. She won over eight multiple songwriting awards including the 2004
VH1 Songwriting Contest, the Gibson Guitar
Dallas Songwriting Contest for "Stand in Line" and the grand prize in the 6th
Great American Song Contest for her song "Impossibility". Jenna continued onto becoming a Finalist with her song, "''Killin' Me
," in the largest International Songwriting Competition'' in the world, known as the
"ISC." Here writers compete from over 11,000 entries from 77 countries. "Killin' Me," eventually went on to become her first radio Billboard radio charting single. But these songwriting awards are what caught the attention of TAXI music CEO Michael Lakow which led to "Just Like That" being produced by the legendary
Nile Rodgers. This song was additionally adopted as the battle song for the 2004 World Series Champions, the
Boston Red Sox using the
"Just Like That Sports Theme" which was included on the Album CD. 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 (Where Did I Go Wrong)" 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. Even the renowned music critic for the
Houston Chronicle, Joey Guerra, describes "Killin Me" It became her most successful single on Billboard's Hot Dance Airplay In fall 2008,
Robbins Entertainment released her single "All Out Of Love" which was played by both
Hot AC and
Soft AC radio stations across the country. With a review feature from Chuck Taylor at
Billboard Magazine on May 17, 2008, 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 (720p) 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, Chris Willis, 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" which became a long-standing summer theme song for the nation's longest running Billboard reporting Dance Station in the U.S., Seattle C89.5. She even beat out Jessie J when hosting the C89.5 Seattle "The Morning Showdown." 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 Seattle Washington, D.C. Chicago, Providence, Houston, Ft. Lauderdale, Phoenix, 2010 Flagstaff, and Minneapolis. ==Billboard chart performance==