Her fifth album proved jazz vocals could still command Grammy attention in an industry moving elsewhere.
By 1999, Diana Krall had already established herself as a pianist-vocalist with serious chops and crossover appeal. When I Look in Your Eyes arrived at a moment when jazz was becoming harder to place on mainstream radio, yet this album managed to reach listeners who might never have bought a jazz record otherwise. The album won two Grammys at the 42nd Grammy Awards — Best Jazz Vocal and Best Engineered Album, Non-Classical — and was nominated for Album of the Year, a category that hadn't recognized a jazz album in 25 years. That kind of recognition matters less for what it says about the music's quality than for what it says about who was listening.
Krall's approach here is direct and intimate. She's a capable pianist, and the production choices favor clarity over flash. The songs themselves — standards and a few newer compositions — sit comfortably in her range, and she doesn't oversell them. What distinguishes this album from her earlier work is how much space she gives the material to breathe. There's no pretense to innovation; she's simply a singer and pianist doing right by the songs. AllMusic gave it four stars, which feels about fair — it's a solid, well-made record that does what it sets out to do.
The album's commercial and critical success came at a specific moment in jazz history, when the form was fragmenting into niches. Krall's accessibility helped her music reach beyond the jazz audience proper, something that wouldn't have happened without the polish and restraint on display here. This isn't a record that jazz musicians debate as a landmark, but it mattered commercially and culturally in a way that pure jazz records often don't.