Satirical rappers, “Saturday Night Live” skitmakers and filmmaking threesome the Lonely Island (comprising Andy Samberg, Jorma Taccone and Akiva Schaffer) have a long history enticing big-name stars into unusual situations, whether it be Natalie Portman quoting Eazy-E or T-Pain discussing mermaid sex. Yet for the lead-off single from album “Turtleneck & Chain,” which hit No. 3 on the Billboard chart in May, the group forged their most unlikely partnership to date, coercing crooner Michael Bolton to sing some choice phrases from “Scarface” for their “SNL” digital short, “Jack Sparrow.”
“(Bolton’s) music is not really meant to be funny,” notes Samberg of the collaboration. “The only real negotiation we had was over what he was comfortable saying. We went through a few different versions ranging from tame to not tame at all, but I think the one we settled on was the best version.” Beyond Bolton, the trio’s latest digs deep into rap’s back pages, including production work from no-nonsense beatmakers No I.D. and T-Minus. Although Taccone cautions, “I would never consider myself a real rapper,” he does take pride in sneaking esoteric references to the likes of Flatbush Project and Mobb Deep amid all the motherloving.