Why You'll Love This
A road trip about wine that's really about a man quietly falling apart — and somehow it's hilarious.
- Great if you want: a character study wrapped in male midlife crisis and pinot noir
- The experience: loose, boozy, and darkly comic — like the trip itself
- The writing: Pickett writes Miles's self-pity with savage, unflinching honesty
- Skip if: you find self-destructive, unreliable protagonists more draining than compelling
About This Book
Two men drive north from Los Angeles into California wine country, ostensibly to drink well and play golf before one of them gets married. But beneath the pinot noir and bad decisions, Sideways is really about the quiet devastation of a life that hasn't gone the way you planned. Miles Raymond is funny, self-destructive, and achingly recognizable—a man using friendship, wine, and forward motion as substitutes for confronting what he's lost. The stakes feel low on the surface and enormous underneath, which is exactly what makes the book hard to put down.
Pickett writes with a loose, confessional energy that suits his narrator perfectly—Miles is verbose, opinionated, and unreliable in ways that feel true rather than clever. The road-trip structure gives the novel natural momentum while allowing it to stop and breathe in moments of unexpected tenderness. Pickett has a genuine feel for the California landscape and an even sharper feel for male friendship: its loyalty, its avoidance, and its limits. The comedy and the melancholy arrive together, the way they do in real life.