Lookout For Shorts

An arrest and conviction for trafficking ecstasy can lead to comedy. The character-strewn path of corrections that followed is entertaining and enlightening.
Lookout is a departure from hardcore prison tales - gonzo and humorous in tone. Picture the worst cruise ship imaginable, that's full of guests from The Jerry Springer Show and never reaches a port. This story focuses on inmate and administrative follies and the coarseness of lockup culture. The author is also serious and introspective at times, unflinchingly detailing his drug-dealing days, a rehab stint, and his misspent youth.
We've all heard of Orange Is the New Black., the fish-out-of-water story that provided a glimpse into a fascinating, under-examined micro-society. Such is the case with Lookout for Shorts, which zips several steps further into humor. This memoir is unique to Oz and other hardcore jail tales, although violence and danger are detailed. The main hazard was the author's head possibly exploding from his immersion in a sea of weirdos and misfits.
Culled from copious, detailed prison journals, Lookout for Shorts is a social study of a curious culture and the institutional ineptness that runs it. This is how the other other half lives and the author's hard-earned cynicism is a comical delight. "If you ever wanted to be the smartest person in the room, just go to state prison for a while. You'll probably be that guy the whole time you're there," quips the author, in Sedaris-like style. Along the way, he ends up deeply-empathizing with his downtrodden fellow felons.
Most of this brilliantly-documented cautionary tale is prison-based, but the story begins with the arrest of a Generation X slacker for dealing drugs at a jam band concert. The reader learns about a stint at an upscale rehab, halfway house living while broke, and finally a thirty-five-month minimum-security bid. The author also examines his underachievement milieu and drug dealing days, and his overarching wish to finish his prison sentence with all of his teeth intact and no new scars.
From the author:
"I spent most of my life lying around, killing time, which led me to a prison term, where I lied around, killing time. The main reason I ended up in prison was a lack of dedication, patience, and my failure to postpone gratification. So after prison, I wrote a book, which requires enormous amounts of dedication, patience, and postponing gratification. It's a start."