"Dry Land" follows Pittsburgh Pirates fans as they navigate the longest streak of losing seasons in the history of major American pro sports. The Bucs' 20-year drift raises provocative questions about why we root for sports teams in the first place. Why would fans invest emotionally in a team with so little to offer? And why do fans who openly describe themselves as "masochistic" and "delusional" stick around?

Charlie Wilmoth chronicles the losing streak and explains how the Bucs finally built a team strong enough to challenge it. Meanwhile, he profiles fans in their teens and twenties...