It’s not every day a Yale student releases a rap album. Actually, I’m not sure that’s happened at all this year, which makes Jacob Sandry’s “Yale Demo” a noteworthy event for the University’s music scene. In just five tracks, Sandry—who records under the name “Yaakov”—covers an impressive range of styles and many of life’s biggest questions. In the end, though, his search for answers and for a flow that fits makes “Demo” an interesting but frustrating debut.

The album’s rap tracks, written over Sandry’s 2010-11 gap year, delve into Ivy League isolation, suburban-housewife ennui, and the meaning of life. None of these are new topics, but Sandry’s verses sometimes call a new image to mind – in “Terminal”, he notes that people around him “put reality in a cage so the world won’t bite us.” Sadly, these original moments get lost in the midst of cheesy lines like “FOX News makes you mad/half-hour long rant” and “you’re forgotten about/let down and left out/with no friends to help those doubts”.

Sandry is a decent rapper and sticks close to his simple, piano-led backing tracks, but his voice isn’t suited to more melodic moments such as the chorus on “Stay at Homeless”, and the Bostonian accent at the end of “Dirge For a Mirror” is confusing, to say the least.

That same “Dirge”– a spoken-word piece written with the help of Sandry’s fellow Teeth slam poetry group – is the closest thing “Yale Demo” has to a mission statement. Sandry’s childhood memories of hiding from monsters under a blanket (featuring the memorable line “I could chill with the Tooth Fairy instead”) shift abruptly to his nights alone, facing the mirror in his “stale bathroom” and wondering “what the fuck have I done today?” Sandry can’t answer that question any more than he can solve the problems of the tired housewife in “Homeless”, but here he’s at least willing to grapple with his concerns in a serious manner. His conclusion, “I want my monsters back,” was actually sad to hear – the piece packs a potent emotional punch.

In an interview, Sandry explained that he hadn’t intended the final line of “Dirge” as an actual answer – the piece, like the album as a whole, was intended to question how we’ve become “so naturalized to a normal life.” He plans to release a full album in the future, something more “holistic” and thematically unified – by then, I hope he’ll have come closer to a solution.

If Yaakov’s move to “pioneer the genre of sexy abstract political folk rap” appeals to you, give “Demo” a listen. If it doesn’t, stick to the last track, “Sailing Down the Speedway.” A tribute to the light-speed Minnesota rapper “Eyedea”, “Speedway” features a chilly, relaxing electronic pulse and 60 seconds of semi-comprehensible rhymes: my attempt to transcribe one section came out as “Ihitthequiddictchcountryspirtmircalsinbtoiwshigtsnosbwel”. Sandry is remarkably good at this pace, and deserves at least a minute of your time.

You can stream “Yale Demo” for free at