By the dawn of the 21st century, Chris Isaak had begun to extend beyond the recording studio and onto the television screen.  In 2001, he launched THE CHRIS ISAAK SHOW, a fictionalized sitcom on Showtime in which he played an exaggerated version of his stage persona, navigating the music industry and comedic hijinks with his real-life bandmates as co-stars.  The show ran for three seasons and showcased Isaak's natural comedic timing and self-effacing humor, a terrific supporting performance by Kristin Datillo as his manager, and cool concert sequences with Isaak and his band and guest performers like Cyndi Lauper, Stevie Nicks or Brett Michaels.  Viewers discovered what concertgoers had long known: behind the brooding balladeer persona, Isaak is a born entertainer and a goofball, never above a tongue-in-cheek joke at his own expense. 

When Isaak returned to new music with ALWAYS GOT TONIGHT in 2002, it felt like a conscious effort to see if his career could pivot toward a more muscular, chart-friendly direction, perhaps helped by his high profile on the Showtime series. To that end, he enlisted commercial-minded producer John Shanks, known for hitmaking work with artists like Melissa Etheridge, Sheryl Crow, Michelle Branch and Bon Jovi.  The result was slicker, shinier, and not always for the better.  The worked-over lead single 'Let Me Down Easy' is a prime example of a kind of late-career minor misstep: straining for radio relevance, it leans too hard on falsetto, edging a generally pretty song into slickly produced conventionality nearing self-parody.

And yet, the same album gives us 'Worked It Out Wrong,' another falsetto-driven ballad - but this one is astonishing.  Isaak croons his heartbreak in minor keys with the same quiet devastation he always has, delivering a song that wouldn't dream of climbing a chart but stands as pure, unvarnished art.  The album also contains 'Life Will Go On,' a melancholy mid-tempo standout that ranks among Isaak's finest late-night laments.  With its soulful chord progression and Isaak's voice lifting into a falsetto plea in the chorus, it proved that even without Erik Jacobsen at the board, Isaak could still strike emotional gold.  And then there's the unhinged charm of 'Notice the Ring' - a rare Isaak rave-up studio track that manages to capture some of the antic energy Isaak brings to his live shows.

While the slightly glossier production - polished guitars here, a programmed beat there - marked a shift in texture, ALWAYS GOT TONIGHT did little to change Isaak's status as a beloved cult figure; its sales weren't any more impressive than usual.  But it closed out his original run at Reprise reasonably, a reminder that Isaak, even when slightly off-course, was still unmistakably himself.

In addition to his Showtime sitcom, he hosted THE CHRIS ISAAK HOUR in 2009 on the Biography Channel - a relaxed, music-focused interview series where he chatted and performed with legends like Nicks and Glen Campbell.  His growing TV commitments continued to sap some of the momentum from his recording career.  In 2006, Isaak released his GREATEST HITS, a perfectly serviceable collection that leans a bit too heavily on radio-friendly falsetto numbers at the expense of the moody, eccentric curlicues that make his albums so memorable.  The compilation showcases his chart ambitions - both realized and not - but doesn't quite capture the full range of his strange, shadowed charm.  Still, it's not without surprises: his out-of-left-field cover of Cheap Trick's 'I Want You to Want Me' is a high-energy gem.

Then came MR LUCKY in 2009, a record that showed Isaak aging fairly gracefully into his role as an elder statesman of heartbreak.  Among its highlights are the gorgeous 'You Don't Cry Like I Do' and 'The Best I Ever Had,' a buoyant, up tempo track that, if I may brag for a moment, I may have personally helped rescue from obscurity.  Originally released as a non-album B-side to 'Let Me Down Easy' back in 2002, it vanished quietly - until I met Isaak after a concert in 2007 and told him it was one of his best songs.  Two years later, it finally made the album.  You're welcome, world.   

In 2011, Isaak paid direct tribute to his musical roots with BEYOND THE SUN, a covers album recorded at the legendary Sun Studios in Memphis.  A long-gestating labor of love, it should have been a heartfelt homage - lovingly made, clearly sincere, yet too often dull, mimicking the originals without much wit or freshness.  Sort of a BAJA SESSIONS 2, which no one needed.  While it would be too simple to say Erik Jacobsen was missed – he was behind the similarly imperfect BAJA SESSIONS - it might have helped to have a strong hand work with Isaak, who may have been too reverent to the material to do anything odd or unique with it.  And yet, flashes.  His version of Jimmy Wages' obscure rockabilly stomper 'Miss Pearl' is electric - raw, joyful, and alive in a way the rest of the album rarely matches.  He doesn't just sing it, he inhabits it, letting loose with a grin in his voice that you can actually hear.  Covers like 'That Lucky Old Sun' offer something more interpretive, showing Isaak's gift for restraint and atmosphere, and even the hardly surprising 'Can't Help Falling in Love With You' somehow floats.  For its missteps, BEYOND THE SUN reminds us that even when Isaak loses the plot, he can still deliver a moment that stops you in your tracks.

Isaak's most recent studio album, FIRST COMES THE NIGHT, arrived nearly a decade ago, and traces of his old darkness still flicker at the edges.  The deluxe edition bonus track 'Some Days Are Harder Than the Rest' brims with tortured angst, while 'Reverie' is a gorgeously haunted ballad, well worth seeking out.  But in recent years, Isaak has seemed increasingly drawn to a different kind of mood: CHRISTMAS.  In 2022, he came full circle of sorts with EVERYBODY KNOWS IT'S CHRISTMAS, his second holiday album following 2004's Christmas.  On these records, Isaak applies his potent voice to seasonal standards like 'White Christmas' alongside self-penned originals, revealing a softer, more wholesome side of his persona-far removed from the seedy, after-midnight melancholy that made his best work shimmer and ache. And I may add, rather less compelling.

At this point, it's looking increasingly likely that we may never get another full album of twelve new songs steeped in heartbreak and quiet devastation - and that's okay.  Chris Isaak's career remains a model of artistic coherence and integrity.  He carved out his world early on, and instead of chasing trends or reinventing himself for reinvention's sake, he stayed true to the aching mood and noir romance that made his best work so singular.  If the curtain has quietly fallen on his studio albums, it only underscores how complete, and how deeply felt, that body of work already is.

He found his lane early - at the crossroads of rockabilly and broken-hearted crooning - and never strayed, choosing to mine that emotional terrain deeply rather than chase passing trends.  The result is a discography with rare emotional continuity.  You can line up SILVERSTONE (1985) and FIRST COMES THE NIGHT (2015) and hear the same artist, guided by sincerity and a singular vision.

Chris Isaak remains a singular figure in American music.  He inhabits a niche entirely of his own - post-modern late-night noir rockabilly heartbreak - and after all these years, he is the king.  The moment you hear that twang of guitar and his voice aching, "I never dreamed that I'd meet somebody like you ...," you know exactly where you are.  He may have never become a conventional superstar, but Isaak has crafted one of the most emotionally rich and consistent discographies in modern rock.