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I have a scene where a character is recounting their side of a story in a courtroom. The character tells a good chunk of their story, and then we see the experiences he is recounting instead of his testimony itself. How would this be best formatted in a screenplay? The scene would cut back and forth several times between the character telling the story and the actual story unfolding. Is each transition a call for a new location? A whole new scene?

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In essence, for every "flashback", you would would have to be a new heading, to reorient the reader as to where we are. However, for going to back to "reality", you can simply use BACK TO SCENE, as so:

Back to scene

The strength of this, is that while you're "in" the flashback, you can easily switch locations, and do whatever it is you wish. When you are done, BACK TO SCENE should always bring back to the courtroom.

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I would highly recommend you watch Akira Kurosawa's Roshomone which does this exactly, multiple times (Much of the film is based on various characters recollecting the same event (the murder of a samurai) from a different perspective. While a few flashbacks are only given once, these are the established facts which all parties agree on. The final moments are all in dispute and are told in a reenactment based on what the character is presumed to testify in court.

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