The Drink ‘Em Both Up achievement and trophy in Alan Wake Remastered is awarded for playing the Coconut song twice on the jukebox. The first instance is difficult to miss. The game’s camera shifts to one of the Anderson brothers asking Alan to put the song on as he makes his way through the diner.
The jukebox is sitting in the diner’s corner just behind the pleading Anderson brother. The second instance, however, is much easier to miss. During the game’s fifth episode, officer Sarah Breaker witnesses the darkness for the first time in the police station.
Sarah and Alan leave Barry behind to makes calls at the station while they head to a helicopter to find Cynthia Weaver. The first stop on this tour is the local town hall. After fighting through a few Taken, you’ll come across a blockaded street. Sarah leads you toward the right side of the blockade near the body of water. The diner sits at the left of the blockade.
Ignore Sarah for now and enter the diner. Once inside, all you need to do is interact with the jukebox. After the jukebox starts playing the song, the Drink ‘Em Both Up achievement and trophy pops.