By and large the Tootsie Roll is the tamest entry on this list and a good way to ease into the experiment. This cocktail was invented for the episode "Slutty Pumpkin" of the first season of How I Met Your Mother. The Slutty Pumpkin created this drink at Halloween and claims it "tastes like an alcoholic Tootsie Roll." The man-child in me insists on renaming it "Impossibly Awesome." The adult-man part of me says, "You already had me at 'alcoholic'; I don't even need to hear the rest."
20th Century Fox Television
Ted: "So, we're at the bar and I see her mix Kahlua and root beer. A cocktail she invented herself. And she called it the Tootsie Roll, because it tastes like an alcoholic Tootsie Roll."
1 part Kahlua
1 part root beer
Since there are no official measurements for this drink, I decided to just fill my glass with half Kahlua and half root beer. Your measurements should be done with the utmost precision.