(March 17, 2023).  It’s been more than 26 years since both 2Pac (Tupac Shakur) and Biggie (Christopher Wallace, a/k/a The Notorious B.I.G.) were gunned down in drive-by shootings by unknown assailants in September 1996 and March 1997, respectively.

With neither rapper living to see his 26th birthday, that means that both Pac and Biggie have now been dead longer than they were alive, a sad commentary for two extraordinary talents whose lives and careers were cut short amid a rivalry that needlessly pitted one against the other and sparked a coastal hip-hop war that didn’t end until both men were gone.

This album was the source material for posthumous hits by rival rappers 2Pac and Biggie

This week, Bobby Caldwell, the legendary soul singer who likely had no stake in hip-hop’s civil war and whose first album came a year before the Billboard chart even saw its first rap single entry in 1979, passed away at the age of 71.  Official cause of death was not provided although the soulful crooner was reportedly suffering from a rare autoimmune condition.

It turns out that the three men—Caldwell, 2Pac and Biggie—are forever linked by that first album, What You Won’t Do For Love, and a couple of hit samples/interpolations that propelled posthumous singles by the two rappers within months of each other.

Here’s the story.

Bobby Caldwell (1951-2023)

Unlike the two late rappers, Caldwell, who is well remembered for his biggest hit single, “What You Won’t Do For Love,” the title track from that 1978 debut album, isn’t in the Rock and Roll Hall of Fame.  In fact, you’re likely not to see him on any GOAT lists—that’s just how underrated (and under the radar) Caldwell remained throughout his decades-long career.  

But that didn’t stop him from being a go-to source for many rap producers in the 1990s and beyond.  His songs have been sampled by dozens of rappers at least 86 times, according to the website WhoSampled.com.  Caldwell clearly was no stranger to hip-hop. 

Both 2Pac and Biggie mined Caldwell’s debut album to come up with tunes that were released posthumously by each rapper in the late 1990s.  And both of those songs revealed the sensitive sides of the one-time pals who were better known for their boisterous and adversarial (often towards each other) images.

In The Notorious B.I.G.’s case, the song was “Sky’s The Limit,” a mid-tempo rap ballad recorded for his sophomore album, prophetically titled Life After Death.  That song, which featured the then-popular group 112 (Biggie’s Bad Boy Entertainment label mates at the time) on the hook, was the most sensitive track on the album that would be released within weeks of the gregarious rapper’s untimely murder.

Given those circumstances and the song’s somber mood, it was the one track on Life After Death that could stir emotions (and did so in my case) on first listen.  The lyrics told Biggie’s short life story, a rags-to-riches tale delivered in three verses where he ultimately denounced the drug-dealing lifestyle he led in his youth and relished the spoils of the rap career he was now enjoying in his young adulthood.

In five-and-a-half minutes, Biggie had acknowledged his past, in vivid detail as only he could tell it, and offered hope for the future, a future that had already been cut short by the time we first heard the song in April 1997.  Adding to the song’s heartbreak was a narrated intro that depicted the slain rapper’s mother cautioning him about the dangers that awaited him if he had kept up his earlier drug-dealing ways.  

But it was the musical backdrop that really set the sad tone for “Sky’s The Limit.”  The music was sampled from Bobby Caldwell’s “My Flame,” a soulful mid-tempo track from that first album, What You Won’t Do For Love.  It was an obscure tune and an unlikely source for a track by the biggest name in rap at the time.  But it certainly worked in providing the perfect setting for Biggie’s story, and made it one of his most memorable songs. 

Below are audio/video clips from both “My Flame” and “Sky’s The Limit.”  Fans of Biggie’s hit will immediately notice the looped instrumental portion of Caldwell’s song from the first few bars.

The album Life After Death went on to reach No. 1 on the Billboard 200 in April 1997, just over a month after Biggie’s death.  “Sky’s The Limit” was the last single released from the album and reached the top 30 (No. 26 on the Hot 100) in January 1998 (along with its flip, “Going Back to Cali”).

Just one week after Bad Boy issued “Sky’s The Limit” as a single, 2Pac’s label released his second posthumous album, R U Still Down (Remember Me?).  And, in an odd coincidence given the motherly reference contained in Biggie’s song, 2Pac’s album was released on his own mother’s imprint, Amaru Entertainment, under Interscope Records’ distribution.  

The R U Still Down album contained tracks Pac had recorded between 1992 and ‘94, which had been intended for an album under the Interscope label before the mercurial rapper unexpectedly signed with Death Row Records in ‘96 after then-CEO Suge Knight posted Pac’s bail following his incarceration on sexual assault charges.

One of the songs on R U Still Down was “Do For Love,” a mid-tempo track that contained an obvious interpolation of Caldwell’s biggest single, “What You Won’t Do For Love.”  Like the original singer’s earlier hit, 2Pac lyrically lamented over a failed relationship and how love had blinded him to all of its red flags, but admitted that there was nothing he wouldn’t do for love, even if it meant swallowing his pride and going back to his erstwhile lover.

Similar to Biggie’s Caldwell-infused song, “Do For Love” was given a somber treatment with a vocal hook by a featured singer from one of the hottest R&B groups at the time, BLACKstreet.  That group’s lead singer, Eric Williams, sang the familiar title line that had made the original so memorable.

Also similar to Biggie’s song, “Do For Love” made strides on the chart and became a top-30 hit, climbing to No. 21 on the Hot 100 in March 1998.  And like Biggie’s album, R U Still Down was a huge seller, moving more than half a million copies in its first week of release.  

Here are clips of the original Caldwell hit and 2Pac’s interpolation, which also contained a prominent sample of another hip-hop track: Pharcyde’s “Y? (Be Like That).”

Both Biggie’s “Sky’s The Limit” and Pac’s “Do For Love” were certified gold (500,000 singles sold) and both properly gave Caldwell songwriter credits.

But the similarities in each song’s history—their concurrent chart runs, top-30 chart performances and gold certifications; their somber moods, their motherly ties, and their posthumous circumstances—are underscored by the fact that both slain rappers had dipped into the sonic well of Bobby Caldwell’s first album to mine mid-tempo tracks that are now part of all three men’s legacies.

May they all continue to R.I.P. 


DJRob (he/him/his), who still believes Biggie was the greatest rapper of all time, is a freelance music blogger from somewhere on the East Coast who covers R&B, hip-hop, pop and rock genres – plus lots of music news and current stuff!  You can follow him on Twitter at @djrobblog.

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By DJ Rob

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