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September 19, 2013
There are a total of 50 Under the Bridge Aerial Challenges in GTA V.
Completing all of them is required for the "Close Shave" trophy or achievement and also counts towards 100% game completion.
First off, get a Maverick helicopter from the South Los Santos hospital helipad. If the Maverick doesn't spawn, go down to the street and up to the helipad again. You can complete all 50 Under the Bridges with it. Most of them are really quite easy. There are just a few hard ones. You might also want to max out the "Flying" statistic of one of your characters first. You can do that by completing the Flight School.
If your helicopter gets massively damaged, you can use the quick save and immediately reload the game. It will automatically be repaired when loading the save game. Also make use of quick save before attempting the harder Under the Bridge challenges.
To make a challenge count you may not touch the ground or any part of the bridge at all while flying under it! If you have done it correctly you will be notified and a collectible tracker will show up on the screen.