No Diggity...Some Doubt

Teddy Riley believed in his future New Jack Swing classic, but nobody else did. Big-ass New Jack Swing playlist included.

Teddy Riley is widely recognized as the father of New Jack Swing, that glorious fusion of down-tempo hip-hop, R&B, and dance pop that ruled the charts in the late ‘80s and early ‘90s.

Teddy's greatest achievement is almost certainly “No Diggity.” Today, the tune is rightly regarded as the perfect marriage of New Jack Swing and G-Funk. And yet, when Riley first composed the future chart-topper in 1996, nobody wanted it.

But this story starts 25 years earlier, when an aspiring songwriter and factory laborer named Bill Withers struck gold.

Bill Withers—Grandma’s Hands (1971)

When soul legend Bill Withers released his full-length debut on Sussex in 1971, he was working as an assembler for the Weber Aircraft Factory in Burbank, California. In fact, the cover photo for Just As I Am was snapped right in front of the plant, while Bill was on his lunch break. You can see his lunchbox in his right hand.

Even as his first record hit the shelves, Withers remained in his day job. He was skeptical of the music business. He did receive a major boost with production from Stax legend Booker T. and prominently-featured guitar work from Stephen Stills. But more importantly, his debut proved a revelation, announcing the arrival of a major talent. Right out of the gate, Bill’s voice was rich with experience; his pen flowing with personal stories.

“Ain’t No Sunshine” was the album's breakthrough hit, reaching #3 on the charts.

Bubbling just beneath it was “Grandma’s Hands.” Bill’s grandfather, Gracchus Monroe Galloway, had been born into slavery in 1855. His grandmother Lula, born a decade later, would frequently bring young Bill to church. These weekly trips were a formative influence on his singing and songwriting.

Bill’s tribute to his grandmother reached #18 on the charts.

The album produced a third single called “Harlem,” which failed to chart.

It does, however, provide the perfect segue for our purposes.

Saturday Night in Harlem (1972)

Just as Bill Withers was burning up the charts, a young child prodigy named Teddy Riley began playing instruments in his Harlem church. His uncle owned a famous Harlem club called The Rooftop, which included its own studio.

Riley spent most of his time here. By his teens, he was lending his beats to visiting artists. In 1986, he produced his first hit, a minor independent chart entry for Kool Moe Dee called “Go See the Doctor.”

Trigger warning: "Go See the Doctor" is about STDs, and it's not a pleasant listen.

New Jack Swing Takes Control (1986)

The same year that Riley pushed Kool Moe Dee into the fringes of the mainstream, Janet Jackson enlisted Jimmy Jam and Terry Lewis to produce her third studio record, Control.

Jam and Lewis spent the first half to the decade hanging with Prince as members of Morris Day and The Time. With Janet Jackson, they would establish themselves as a major production team.

On Control, they married their native Minneapolis funk sound to an emergent blend of hip-hop and R&B. The record’s synthy syncopation would become a trademark of New Jack Swing.

Producing a remarkable five Top 5 Hits, Control moved Janet Jackson into the epicenter of pop music, and proved a landmark in the mainstreaming of New Jack Swing.

The Rise of "Urban Contemporary"

This “urban contemporary” sound--as it was labeled by radio programmers--was typified by a blend of hip hop sampling, Quiet Storm vocals, and the omnipresent Roland TR-808 drum machine. At the time, it was a bold hybrid. Hard-edged rappers like Public Enemy and NWA stood in stark contrast to the more vulnerable soul singers in the R&B camp.

It was Teddy Riley, more than any other figure, who made peace between these camps.

Peak Era New Jack (1987)

Village Voice is credited with coining the name of this novel hybrid in a 1987 profile of Teddy Riley. It would prove a fitting association. Both as the lead singer of his own New Jack Swing combo Guy—with future solo star Aaron Hall—and as a rising producer, Teddy Riley stood at the forefront of the next big thing.

Over the coming years, New Jack Swing would become more than just a moment in popular music. It was a Black cultural force that was widely embraced in the mainstream, even achieving a brief level of dominance in film, fashion, and humor.

Young artists like Bobby Brown (formerly of New Edition), MC Hammer and Boyz II Men ruled the charts. Established artists like Whitney Houston and Michael Jackson emulated their sound. Television shows like The Fresh Prince of Belair, Arsenio Hall, and In Living Color made music a central part of their identity. The result was a mainstream proliferation of the New Jack sound and style. Parachute pants and box cuts were everywhere.

Renaissance Teddy (1991)

By 1991, Teddy Riley was an in-demand studio mastermind. Guy had splintered, with Aaron Hall pursuing a solo career. Riley joined a star-laden engineering booth with Babyface, Daryl Simmons, and L.A. Reid to help produce Bobby Brown’s third record, Bobby.

Riley produced a duet for Bobby and soon-to-be-wife Whitney Houston called “Something in Common” but the album’s most notable moment was #3 hit “Humpin’ Around.”

That same year, Riley manned the booth for Heavy D. & the Boys, who landed their biggest hit with a cover of the O’Jays’ “Now That We Found Love.” Featuring guest vocals from Aaron Hall, it reached #11 on the Billboard Hot 100 that year.

Simultaneously, Riley found the time to form two groups—a New Jack Swing combo called Blackstreet and a hip-hop group called Wreckx-N-Effect. The latter would be the first to bring big returns.

The Original Rump Shaker (1992)

By the early '90s, artists like Whitney Houston and Michael Jackson were chasing Riley’s sound—so much so that MJ enlisted him as a co-producer for his 1991 mega-platinum Dangerous. Lighting up the charts in 1992, Dangerous garnered more than 30 million in sales. This technically qualifies it as the biggest selling New Jack Swing record of all time.

The same year, Riley nearly topped the charts on his own merits. Riley was both the producer and featured rapper on “Rump Shaker”.

The #2 hit was powered by a sample of the Lafayette Afro Rock Band’s “Darkest Light”.

Only Whitney Houston’s towering “I Will Always Love You” kept Wreckx-N-Effect from the top spot.

Fortunately for Riley, his biggest hit was still ahead.

No Diggity—Blackstreet feat. Dr. Dre and Queen Pen (1996)

In 1995, Montell Jordan reached #1 with “This is How We Do It," driven by a Slick Rick simple with enhancements from Teddy Riley. It was the ultimate mainstream moment for New Jack Swing, knocking Madonna's "Take a Bow" from the top spot on the Billboard charts, and holding the slot for 7 consecutive weeks in the spring of '95.

It would also be something of a last gasp for the Golden Age of New Jack Swing. It was now the mid-'90s. The Boy Band era would soon be fully upon us.

So that may explain the lukewarm reaction Riley received from his colleagues when he came up with “No Diggity,” a quintessential down-tempo New Jack Swing tune built on a sample from “Grandma’s Hands” by Bill Withers.

At the time, Riley was in the midst of a reunion tour with Guy. He suggested the song to his bandmates. There weren’t interested.

He then offered it to Aaron Hall as a solo vehicle. He wanted nothing to do with it.

He then proposed the song to his bandmates in Blackstreet. According to Riley, “None of the guys liked 'No Diggity'. None of them. They would even say it.”

This, says Riley, is the reason that his voice is the one heard most prominently on the recording. He recalls being forced up front in the mix because he was the only one who actually believed in the tune.

Of course, it helped that he enlisted Dr. Dre for a verse. By 1996, Dre was widely recognized as a key architect of the G-Funk sound. Like New Jack Swing, G-Funk sparked its own pivotal mainstreaming of Black culture. In many ways, "No Diggity" was the bookend on their shared decade of dominance. Merging Dr. Dre's laid-back So-Cal drawl with Riley’s New Jack grooves yielded a pinnacle moment for both sounds.

Toss It Up—2Pac feat. Aaron Hall (1996)

Tupac Shakur disagreed.

Blackstreet’s “No Diggity” was released on July 29th, 1996.

Tupac was fatally wounded during a drive-by shooting in Las Vegas on September 13, 1996.

On September 26th, 1996, Tupac’s posthumous fifth studio album was released under the stage name Makaveli. It contains a track called “Toss It Up” which includes explicit musical copping from “No Diggity” and a ton of shade thrown in Dr. Dre's general direction.

Remarkably, Aaron Hall provided vocals for Tupac, consciously spoofing the song he rejected earlier in the same year.

The Aftermath

Whatever Tupac and Aaron Hall felt about "No Diggity," it was a universal smash. Not only did it reach #1 on the Billboard Hot #100 in November of 1996, but it mercifully ended a 14-week Reign of Terror atop the charts for “Macarena” by Los Del Rio. (audio clip intentionally excluded)

“No Diggity” would go on to sell more than 1.5 million copies on its way to the 1998 Grammy Award for Best R&B Performance by a Duo or Group with Vocals (which is a stupidly long name for an awards category).

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"No Diggity" is also the inspiration for the bonus playlist below, a melange of Clinton Era gems that take me right back to every high school dance ever. Two important user notes here: This playlist is NSFW and it is meant to be played on shuffle.