“Never cried about a lack of press, rather be a dope failure than a wack success” Droog explains on the opening MetroCard swipe “Stillwell Baby.” The track is a fantastic transition from a The Elgins sample where “life is so lonely without you,” as the car switches tracks and allows Droog to gently rise through this grogginess in his rhymes. Already a heavyweight through lyrical ability, Droog uses the production from skywlkr as a warm-up that eventually moves into a less somber, more upbeat style of track. “Stillwell Baby” is important to highlight though, as the first track on Transportation contains more beat transitions and style switches where Droog does batting practice, acting as the Ralph Branca of rhymes.
Transportation feels and behaves as if it was a mature, graduation act to an already developed performance from Droog. As “Monthly” follows, the raging flutes and jazz house percussion pushes the vocals to be rushed but still collected. Never flustered under pressure, Droog punches a clever wordsmith title as he illustrates complex storytelling without becoming overbearing. More of a display from The Purist who produced “Monthly,” Droog pairs well with the instrumentation but never stands on his backfoot as Transportation continues to move without a sense of falling to a stop.
As the terminal seems closer and closer, Droog dismounts from Uptown, cruises through Midtown and then eventually hits Downtown before seeing the mountains of Manhattan sprawling out. Lighting a loosey and stepping off the platform, everything seems to fall into place as Transportation leaves the station and trails off to repeat the whole journey again tomorrow.