Momsen's career slowed for three years until she received the lead role in the never-aired WB series Misconceptions. Momsen appeared in the 2006 film Saving Shiloh and also the 2007 Walt Disney Pictures film Underdog, as Molly. She auditioned for the title role in Hannah Montana, and was in the top three, but the role was instead awarded to Miley Cyrus.
Taylor attended the Professional Performing Arts School in New York City. In 2008 Taylor Momsen starred as Jennifer in the movie Paranoid Park. Beginning in 2007 she played the character of Jenny Humphrey in The CW television series Gossip Girl. Momsen, who appeared in only four episodes through the first half of season four, was then scheduled for an indefinite hiatus from the show.
Momsen has stated that "music is where I can be me," saying that "Acting is easy. I've been doing it for so long and I totally love it. But you're playing a character instead of yourself. Music is more personal because you're writing it and you're involved in every step of it."
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When she was 5, Momsen recorded the song "Christmas, Why Can't I Find You?" for the soundtrack to How the Grinch Stole Christmas. In 2002, she recorded the songs "One Small Voice" and "Rudolph The Red-Nosed Reindeer" for the compilation album School's Out! Christmas.
In March 2009 Momsen stated in an interview with OK! Magazine that her band The Pretty Reckless had then recently signed a deal with Interscope Records. She writes all the songs, sings and plays simple guitar on the album. She played her first tour with her band opening for The Veronicas on their Revenge is Sweeter Tour in spring 2009.
The band's debut album Light Me Up was released on August 30, 2010 in the U.K., where it debuted at number 6, as well as at number 18 in Ireland. The first single "Make Me Wanna Die" was released on May 30, 2010, where it peaked at number 16, while the second single "Miss Nothing" which was released on August 23, 2010 peaked at number 39. The third single released has been "Just Tonight."
Heidi Montag recorded "Blackout," a song written by Momsen. According to Momsen, she wrote the song when she was 8 years old and recorded it as a demo with a producer.
Her video, “Make Me Wanna Die," was held up for legal reasons for a long time because she was 16 when it was made and she stripped off her clothes while strolling through a graveyard. The released version features a relatively more modest, lingerie-clad Momsen walking among the tombstones.
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