And so it came to pass that, in 1986, Lyle Lovett released his finest album, The Road to Ensenada. Lovett’s early albums are so uniformly excellent that it’s difficult to single one out as number one, but Ensenada blends some of his best songs with perfect performances and production and it’s also his most successful marriage yet of the heartfelt and the humorous.
On the heartfelt side, you have several songs inspired by his divorce from Julia Roberts, just a year or so after their unlikely marriage. I remember I was living at home when Lovett and Roberts married and my mother told me the news one morning when I was half asleep. When I made my way downstairs, I had to ask her if I’d dreamed that conversation. It was that bizarre a concept.