Released on Aug. 24, 1999, The Vault…Old Friends 4 Sale is a bit of a sore spot for Prince. He compiled the previously unreleased material years earlier to fulfill his contract with Warner Bros. after a bitter battle with the record label.

The project is a bit of a hodgepodge; three of the songs were originally intended for the soundtrack for James L. Brooks’ 1994 film, I’ll Do Anything. The rest of the tunes were recorded in the early and mid-'90s, except for “Old Friends 4 Sale,” which dates back to 1985.

Like any Prince album, there are gems among the tracks. Overall, the LP documents the NPG and the Hornheads’ talent for jazz-flavored grooves; it’s not surprising that a couple songs made the setlist for Prince’s 2009 appearance at the Montreaux Jazz Festival. However, The Vault…Old Friends 4 Sale has a few weak spots, and its pace might put listeners to sleep before they make it to the closing song, which is quite lovely. Here’s a track-by-track guide.

“The Rest of My Life”
Originally written for the I’ll Do Anything film, this short, schmaltzy ditty could work onscreen, perhaps in the background during the opening credits. It isn’t, however, the strongest choice for the album’s opening tune. It does have an infections piano riff, but Prince could do that in his sleep.

 

“It’s About That Walk”
Prince had very specific requests for women: You don’t have to be beautiful, just give him your extra time. You don’t have to be rich, just plant one on him. And, according to track two on this album, you don’t have to be well-traveled, just have a killer walk. It’s one of the most fun songs in Prince’s repertoire.

 

“She Spoke 2 Me – Extended Remix”
Sometimes, it’s hard to imagine Prince being pleasantly surprised by female attention, but songs like this remind us that he was human and therefore capable of being lovesick — that is, if he’s the protagonist. The tune first appeared in Spike Lee’s Girl 6 film, a soundtrack comprised entirely of Prince songs. If you have a soft spot for the taught, early-90s iteration of the NPG, this extended version should be a treat. It provides just a glimpse of the band’s masterful jamming. The horns are nothing to sneeze at, either. This gem is so good, Prince included it in his critically acclaimed shows at the 2009 Montreux Jazz Festival.

 

“5 Women”
“I ain’t heard no breakup song like I can write,” Prince proclaimed in his memoir, The Beautiful Ones. “I have that knowledge.” Of course, “5 Women” doesn’t come close to the anguish in other songs like “Nothing Compares 2 U.” Still, Prince manages to convey his heartbreak while winking at his womanizing reputation. He recounts his conquests from March through July over a basic blues structure. The song was originally given to Joe Cocker, whose 1991 rendition — inferior by comparison — includes an ambitious key change midway through.

 

“When the Lights Go Down”
If you hadn’t guessed this album was going to have a mellow mood, it should be clear by the end of this seven-minute track. It’s another jazzy tune that Prince pulled out for the 2009 Montreux Jazz Festival, but much looser than “She Spoke 2 Me.” There’s no horn part and the standout features are the hand drums (by either Sheila E. or Kirk Johnson, according to PrinceVault) and Prince’s piano flourishes.

 

“My Little Pill”
After Prince died, people combed through his discography looking for insight into his personal life. Though there is a lot of truth in his music, this interlude-length song was another written for I’ll Do Anything, likely with a character in mind. As odd as the piano tune is, it’s a welcome respite as the album is beginning to drag at this point. Unfortunately, things are about to get even slower and more depressing…

 

“There is Lonely”
Let’s be real; the songs Prince recorded for I’ll Do Anything were not great. This example, an attempt to convey the depths of loneliness, is full of unimaginative lyrics and an uninspiring melody. The guitar solo and Prince’s intoxicating low register almost save it.

 

“Old Friends 4 Sale”
Originally recorded in 1985, the personal, haunting ballad unfolds like a dramatic play. Fans speculated about the cast of characters each time Prince unearthed the track and reworked the lyrics. Ultimately, the song is about a betrayal of trust. While this version employs an impressive, big-band sound and passionate singing from Prince, it lacks some of the intimacy of the original. But it’s a testament to Prince’s ability to reinvent his music over time.

 

“Sarah”
It’s actually surprising a woman hasn’t come forward claiming to be the inspiration for this song. From Marsha to Nikki to Cynthia to Vicki to … er … Billy Jack, real and imaginary women dominated Prince’s music. It’s too bad imagining who Sarah could be is more interesting than listening to the actual song, which is too bad because it’s the first upbeat tune we get since “It’s About That Walk.” It’s a forgettable track, but that makes sense, given it was recorded in early 1996 when Prince’s relationship with the NPG was breaking down.

 

“Extraordinary”
This lush, dreamy ballad is a fitting closing track. Prince almost gave it away to protégé Rosie Gaines, but something tells us she would have done a better job with the material than Cocker did with “5 Women.” Prince’s smooth vocals and harmonies are outstanding. The live version on the 2002 One Nite Alone…Live! album is even better, with Candy Dulfer standing out on saxophone.