Hilary Duff / Melissa Joan Hart
The actress was a solid gold money-making machine as tween Lizzie McGuire, but her film ventures have mostly tanked. So unless her singing career takes off, young Duff seems to be heading down the Melissa Joan Hart path. She may keep working, but it will be in obscurity. (AP / Getty Images)
Shia LaBeouf / Leonardo DiCaprio
Life is looking promising for this young actor who came of age on the family television show Even Stevens. Leonardo DiCaprio came of age on a television show too. Could LaBeouf follow in DiCaprios footsteps? Only time and Martin Scorsese will tell. (Getty Images / AP)
