Perhaps this is just a victory lap for Reeves, but even then, most victory laps aren't as needlessly bloated as this.
If you claim to have more class than Dianne Reeves, then you're obviously a liar.
Sure, jazz-pop divas come and go every passing year, but very few seem to make much of a lasting impact. After all, it's hard when you don't have a compelling back-story like Melody Gardot, or an NPR-ready international appeal like Madeline Peyroux. Yet Reeves has been plugging away at her art since the late '80s, and through all the tribute albums, pop excursions, and guest appearances, it wasn't until 2005 when she really got to reach out and show us she was a genuine class act. With George Clooney's McCarthy/Morrow flick Good Night and Good Luck, though, Reeves was perfectly cast as a fill-in for Rosemary Clooney, her set of period-standards supported by a minimal backing band, resulting in an absolutely fantastic soundtrack that also doubled over as her best disc to date, partly due to the timeless nature of the originals as well as Reeves' own interpretations (it could be played in 1958 or 2008 and you'd still have a hard time pinning exactly what era it's from). It not only introduced Reeves to a wider audience, but it also set up expectations for When You Know -- her first studio album since Good Night -- to be the disc that makes or breaks her mainstream commercial appeal, telling labels everywhere if her audience could carry over from a classy Oscar-nominated film to an album of jazz-pop lullabies.
The short answer, sadly, is no.
What made Good Night such a revelation wasn't just the reverence that Reeves and co. gave the Clooney songbook, but the sheer intimacy of the proceedings, allowing Reeves' inimitable pipes to take center stage and deliver the emotional wallops that the tracks required. With When You Know, Reeves finds herself back in the jazz-pop environment, now with a lush sheen of studio polish, top-notch session men, and swirling orchestral accompaniments filling the larger numbers to the point of excess. In short, Reeves' powerful voice feels positively drowned out in this setting, her highest high notes always sounding subdued in the lounge-y environment. This is most evident on the absolutely overblown production for "The Windmills of Your Mind" -- a song that's already somewhat knotty to begin with -- in which the strings sound like they're fighting for space against the pianos, the tempo switches proving more jarring than cathartic, all while Reeves is trying her darndest to keep the whole thing grounded. This is a sharp contrast to "Midnight Sun", which is blatantly crafted for adult-contemporary radio consideration, the grooves themselves sounding remarkably tired.
Featuring nine covers and one original, When You Know is deliberately going for a classicist kind of vibe, but some attempts fare better than others. The most ill-advised of all is when Reeves covers Minnie Riperton's inimitable disco-era glass-shattering ballad "Lovin' You". Here, the tempo is slowed down, the instrumentation of the original beefed up to no effect, the whole thing sounding as ridiculous as any earnest cover of "Lovin' You" inevitably would.
Tracks like this, however, are forgivable in light of some of the more awe-inspiring moments that Reeves still has inside of her. The disc opens with a well thought-out cover of the Temptations' "Just My Imagination (Running Away with Me)", a simple yet potent tale of unrequited love that's given a strong emotional backbone by Reeves' naïve-yet-sweet vocal stylings. The gloriously understated "Over the Weekend", meanwhile, is one of the most romantic tracks that Reeves has ever committed to disc, riding a slinky guitar line right into the smoky chorus. Stranger still is "When You Know", which somehow comes across as a leftover song from the musical Wicked (which, in this instance, is meant in the most complimentary way).
The final song is the sole original, a bluesy track that Reeves penned herself in tribute to her mother, and it serves as a lively closer to what is, ultimately, an average-sounding jazz-pop record. There are some extraordinary moments to be found, for sure, but Reeves can do -- and has done -- much better. Perhaps this is just a victory lap for Reeves, but even then, most victory laps aren't as needlessly bloated as this.