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Emily Osment on Hannah Montana.
Disney Channel
During an appearance on Friday Night With Jonathan Ross in 2009 Cyrus said that she began auditioning for the show at 11 years old.
The casting directors asked her to read for Hannah Montana, which she did, but they thought she was too young for the role.
She ended up landing the role anyway and by the time the show premiered in early 2006, Cyrus was 13 years old. Meanwhile, Emily Osment portrayed Lilly. 
Cyrus met Gossip Girl star Taylor Momsen during the audition process.
Taylor Momsen as Jenny on Gossip Girl.
The CW
At the time, Momsen was known for roles in How the Grinch Stole Christmas and Spy Kids 2: Island of Lost Dreams. ....

Jason Earles Jackson Stewart , Reese Witherspoon , Cody Linley , Jake Ryan , Lilly Truscott , Emily Osment , Billy Ray , Madeline Martha Mackenzie , Billy Ray Cyrus , Taylor Momsen , Jonathan Ross , Mitchel Musso Oliver , Elton John , Night With Jonathan , Hannah Montana , Grinch Stole , Lost Dreams , Mitchel Musso , Oliver Oken , Kiki Dee , Miley Stewart , Little Lies , Ray Cyrus , Jason Earles , Jackson Stewart , Miley Cyrus ,