View Solution

In order to determine the fate of Brent Backflip, you need to send Wayne De Spiritwhistle and Patrick Bannon through the rooms in the 1st segment in a specific order.

First you send the two of them over to The Prop Store (button with the dumbbell).
Next you send them to The Costume Room (button with the hanger).
Lastly you send the duo to the scene of the accident, The Sound Stage (button with the megaphone).

After this is done, you will unlock the achievement by the first break.

Note that this is the path I took. Judging by the end screen, the only thing that matters might be the last step.