At the age of 17, Gretchen started singing in small bars around St. Louis, Missouri. In 1991, Susie Osburn, a bar manager from Springfield, Missouri, went to St. Louis, looking for a new band for her bar (Townhouse). Susie stumbled upon Gretchen, offering Gretchen the job. Gretchen played at the Townhouse for two years then moved back to Pocahontas. After a failed marriage to former bandmate, Larry Rolens, Gretchen moved to Nashville.
Gretchen started dating Mike Penner. On Novermber 9, 2001, a daughter, Grace Frances Penner, was born to them.
- Here For The Party-This album came out with Epic Records in 2003. The first single coming from this album was 'Redneck Woman'. The song was the first number one hit by a woman in two years. The next single hit coming from this album was 'Here For The Party'.
- All Jacked Up-Came out on September 27, 2005, 'All Jacked Up' (the song) peaked at #8 on the Hot Country Songs. Three more singles came from this album 'I Don't Feel Like Loving You Today', 'Politically Uncorrect' (featuring Merle Haggard), and 'California Girls'. None of the three made it to the Top 20 on the country charts.
- One Of The Boys-This album came out on May 15, 2007. It debuted at #5 on the Top 200 and #1 on the Country album Chart. After 10 weeks, the album went bye-bye from the Billboard Top 200. The first to singles released from this album were 'Come To Bed' (featured John Rich) and 'One Of The Boys'. Both peaked in the thirties on the country charts while the final single 'You Don't Have To Go Home' failed to reach the Top 40.
- I Got Your Country Right Here-Was released on July 14, 2008 with the first single 'Don't Do Me No Good'. The song failed to reach the Top 40.
- Don't Make Me Take My Earrings Out-Came out in March of this year with the release of her song with the same name. The song is also referred to as 'The Earring Song'.
- 2005 CMA Female Vocalist of the Year
- 2004 ACM Top Female Vocalist
- 2004 ACM Top New Artist
- 2004 CMA Horizon Award
- 2004 Grammy Award Best Female Country Vocal Performance