Basically you need to 5 star all scenes in challenge mode, making sure you get the bonus medals too. After collecting all of the medals the achievement will pop.
Tip for people who are having trouble 5 staring the scenes with no teleprompter:
If your cell phone can do voice recording, record yourself in quick play doing the scene with the teleprompter on and make sure you get 5 stars. Make sure to start your recording at the 3. Also play the scene again with your recording to make sure it 5 stars again.
After you record all the scenes you need to then start the challenge. Make sure the press play on 3 or a millisecond delay to start your recording on time. It may take a few tries! Don't give up, eventually you will get it. Took me 6 tries for the hardest 5 scene challenge.