Hoodie Allen, "All About It" (2014)
Though Sheeran and collegiate pop-rap cutie Hoodie Allen were longtime pals, they didn't collaborate until 2014, when they cut this track for Allen's debut studio album, People Keep Talking, in a single night. "We finished the whole song in four hours," Allen told Billboard. "And eight months later, after tweaking the beat nonstop, we had the final version." The sing-song rap style Sheeran adopts here allows him to boast more explicitly about his writing skills than he does in his pop-folk mode, and the video, in which both performers dress like musclebound superheroes, permits Ed to goof around too.