Overtake the leader a second before the finish.
This trophy, like the other miscellaneous trophies, has a medal of the same name which unlocks at the top left of the screen, this one is only at the end of the race. Be in any position and overtake the leader at the very end, moments before the finish line. This is likely to come naturally, more often than not it will unlock with Academy Award. However if it doesn't, it can be done in party mode with 2 controllers very easily. Have one vehicle get to the finish line of a race but do not cross the line, then take the second controller and overtake him and immediately cross the finish with the other vehicle too.