Sideways

Sideways is a comedy-drama film that follows two middle-aged men, Miles and Jack, on a road trip through California's wine country. Miles, an unpublished writer and wine aficionado, wants to spend the week relaxing and enjoying good food and wine. Jack, a former actor and soon-to-be-married man, is on the prowl for one last sexual fling before settling into domestic life. As they visit various wineries and vineyards, they encounter a cast of colorful characters and find themselves in unexpected situations that challenge their friendship and their views on life, love, and relationships. Nominated for five Academy Awards® including Best Picture, this critically acclaimed film features witty dialogue, engaging performances from Paul Giamatti and Thomas Haden Church, and stunning cinematography of the California coastline.

You can stream Sideways on: Apple TV Amazon Store

Some movies that have similar genres and were produced around the same time as Sideways include He's Just Not That Into You, Life or Something Like It, Saving Face, Juno, Lost in Translation, Love Don't Co$t a Thing.