In particular, he transfers the sweeping melancholy of Roy Orbison's classic Monument singles ("Crying," "Oh, Pretty Woman," "In Dreams") to the more stripped-down, rootsy sound of Sun, resulting in a stylized take on '50s and '60s rock & roll that made him into a star in the early '90s, propelled to a great degree by the hit single "Wicked Game."

Isaak began performing after he graduated from college, forming the rockabilly band Silvertone. The group, which featured guitarist James Calvin Wilsey, bassist Rowland Salley, and drummer Kenney Dale Johnson, would become the singer/guitarist's permanent supporting band. Isaak released his first album, Silvertone, on Warner Bros. in 1985. It was critically well received yet failed to sell well. Two years later, he released the self-titled Chris Isaak, which managed to scrape into the Top 200 album charts. After its release, the singer began an acting career with a bit part in Jonathan Demme's 1988 film Married to the Mob; he would later have parts in Wild at Heart, The Silence of the Lambs, and A Dirty Shame, as well as starring in his own situation comedy series for the Showtime cable network.

Released in 1989, Heart Shaped World initially sold more than Chris Isaak, yet it didn't manage to break big until late 1990, when the single "Wicked Game" was featured in David Lynch's Wild at Heart. Soon, the single became a Top Ten hit; the album also made it into the Top Ten and sold over a million copies. Both 1993's San Francisco Days and 1995's Forever Blue mined essentially the same vein as Heart Shaped World, yet both went gold and spawned a handful of hits. In 1996, Isaak released The Baja Sessions; Speak of the Devil followed two years later.

Isaak's busy touring schedule and growing visibility as an actor kept him out of the recording studio until 2002, when he released Always Got Tonight, though in 2004 he did find time to cut his first seasonal album, Chris Isaak Christmas, which featured five new Yuletide tunes along with a batch of holiday favorites.

The musician once again flexed his TV muscles in 2009 with The Chris Isaak Hour, whose debut on the Biography Channel was promoted in part by Mr. Lucky, his first album of original material in seven years. A year later he released the concert album Live at the Fillmore. In 2011, Isaak paid tribute to the classic '50s rockabilly and country music produced by the legendary Sam Phillips at Memphis' Sun Records with his album Beyond the Sun. Recorded at Sun Studios, Isaak delivered cuts originally recorded by such artists as Elvis Presley, Johnny Cash, Jerry Lee Lewis, Carl Perkins, and others.

In 2015, Isaak signed on as a judge on the seventh season of The X Factor Australia. Also that year, he returned with his 13th full-length album, First Comes the Night. Recorded in Nashville with longtime producer Mark Needham, the album also included production from Paul Worley (Dixie Chicks, Lady Antebellum) and Dave Cobb (Jason Isbell). ~ Stephen Thomas Erlewine