Add the chocolate chips, 1/3 cups stout (reserve the other 1/3 cup of stout for the milkshake), and the butter in the top of a double boiler over medium heat.
Stir until the chocolate has melted and combined with the beer and butter (if the sauce separates, use an immersion blender to bring it back to life). Set aside.
Add the crushed pretzels to a bowl.
Dip a serving glass in the chocolate, then the pretzels to rim the glasses.
Add the ice cream plus the remaining 1/3 cup stout to a blender, blend until smooth.
Pour the milkshake into the glass until about half way full, add a few scoops of chocolate sauce on top of the ice cream, then fill the glass with the ice cream mixture.
Top with generous amounts of chocolate sauce, whipped cream, crushed pretzels, cookies and candy.