Welcome back. Last time, we brought you the best, worst, savviest, and weirdest of Def Jam’s first decade. Now, here’s the best of decade two. Starting in late 1994 after the label-saving success of “Regulate,” when the label found salvation through a surprising crooner; and continuing through the end of 2003, when a series of unfortunate events caused two of the label’s biggest artists to fall out of commercial favor—one of his own accord, one not so much. Here’s your tour guide to the second decade of hip-hop’s most influential label.

This Is How We Do It: A Vision Realized (Late 1994–1997)

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Montell Jordan in 1995.

The earliest tensions in Def Jam’s history surrounded R&B. Label co-founder Russell Simmons always had a thing for smooth crooning, and some of the label’s earliest releases, right along the Beastie Boys and LL Cool J, were from singers like Oran “Juice” Jones and Chuck Stanley. Simmons’ then-partner Rick Rubin had no love for that kind of music, preferring thrash metal and punk.

The record-buying public took a while to come around to Russell’s vision as well. Def Jam’s R&B releases were few and far between, and none were massive commercial successes. That all changed when West Coast record biz veteran Paul Stewart brought a singer from South Central LA to audition for Simmons.

Montell Jordan blew Russell away, and he would go on to impress millions more with his debut single “This Is How We Do It,” which shot to #1 and cleared the way for future Def Jam R&B stars like Ashanti, Bobby Valentino, and Rihanna.

Highlight: Montell Jordan - “This is How We Do It”

This song is absolutely unstoppable, from the short a capella intro to Montell’s ad-libs at the end. Bonus points for sampling a key piece of Def Jam’s history, Slick Rick’s classic cautionary tale “Children’s Story.”

Lowlight: MoKenStef - “Sex In the Rain”

Not all of Def Jam’s R&B efforts were as successful as Montell. This confusingly-named group had a hot single with “He’s Mine,” but this draggy follow-up with a cringe-worthy title and concept (and a terrible lyrical pun on “wet dream,” to boot) sabotaged their career before it could really get started.

Curiosity: Richie Rich featuring Tupac – “Niggaz Done Changed”

Also known as “that song where Pac predicted his own death.” Conspiracy theories and he’s-really-in-Cuba stories aside, it is eerie to hear Pac rap, “I been shot and murdered” not long before he really would be shot and murdered.

Big Moves: The Joint Chiefs

By the end of 1997, Def Jam had joint ventures with Chris Lighty’s Violator Records and Roc-A-Fella Records, home to Jay Z. These ventures would shortly pay off big time, as we’ll see below.

It's the Roc (And Some Dogs): Jay-Z and DMX (1998–2000)

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DMX during Woodstock 1999 in Saugerties, New York.

1998 would prove to be a giant year for Def Jam, thanks mostly to two polar-opposite rappers. Jay-Z (who hadn’t yet lost the hyphen) was cool and calculating—the type to sit back, puff on an expensive cigar, and plan world domination. Then there was Earl “DMX” Simmons—a wild man who barked like a dog, drenched himself in blood on album covers, and was as likely to get arrested for animal cruelty as he was to star in a hit film.

Highlight: Jay-Z – “Hard Knock Life (Ghetto Anthem)”

This was the 1998 song that moved Jay from “that dude who did a song with Foxy Brown” to a giant star who everyone wanted to emulate. He remembered the experience on his song “Do It Again (Put Ya Hands Up)” from the following year: “[I] shipped two million, then I blew to three/Then I skated to four, 'fore I went on tour/I came back and it's plain, y'all niggas ain't rapping the same/Fuck the flow, y'all jacking our slang.”

Lowlight: Sisqo – “Unleash the Dragon”

This title track was the only one of Sisquo’s singles on his hit album not to chart, and with good reason. As if the mediocre song wasn’t bad enough, it came along with an interminable seven-and-a-half-minute music video/incoherent Godzilla rip-off (see above, if you dare) that is commonly considered one of the worst videos ever.

Curiosity: EPMD Remakes... Themselves?

EPMD’s mediocre 1999 album Out of Business moved from run-of-the-mill to bizarre once you got to the bonus disc. Labelled a “Greatest Hits,” the album actually featured Erick and Parrish re-doing their old songs, as they couldn’t get licenses from their old label to use the originals. The poorly recorded remakes may well be the lowlight of the legendary group’s career.

Big Moves: Russell Becomes the $100 Million Man

In 1998, PolyGram, who already owned a 10% stake in Def Jam, became part of the corporate behemoth UMG. Part of the wheelings and dealings that followed involved giving Russell Simmons a reported $100 million for the rest of his stake in the label.

It’s Murder!: Murder Inc. and the Continuing Reign of The Roc (2001–2003)

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Ja Rule between takes at a music video shoot in North Hollywood, Calif., in July 2001.

The early aughts saw a triumph of a new model for artists. After groups and DJ/MC pairings faded out and were replaced by solo stars, the next natural step was the development of crews. Loosely related artists—all soloists in their own right, but joined by a common record label, aesthetic, neighborhood, or suit preference—were joining up into crews.

This was not new for hip-hop, of course, but the model had fallen a bit out of favor until it started gaining steam again in the late ‘90s. By the time the 21st century hit, Def Jam was all-in. Their two biggest crews were Roc-a-fella and Murder Inc.

The Roc had, by 2001, turned Jay Z’s success into a stream of releases from their other artists. By 2003, even the Roc’s crew members would have their own crews, with Beanie Sigel from Roc-a-fella bringing out his own State Property camp, and Cam’ron leading the Diplomats. Murder Inc., led by brothers Irv and Chris Gotti (née Lorenzo), began having success with their flagship artist Ja Rule back in 1999, but it wasn’t until his 2001 album Pain Is Love that he turned into a #1 single having, Grammy winning sensation. He was soon joined by Murder Inc.’s first lady, singer Ashanti.

Def Jam also turned its eyes towards the South. The success of Ludacris’ debut album led to Def Jam South, which began in 2000, blowing up—though it would shut its doors at the end of this era.

Highlight: Scarface – “My Block”

This powerful ode to Face’s neighborhood is one of the most perfect slices of hip-hop ever committed to wax. It is full of love, but there are hidden undercurrents of anger at the system that keeps his block the way it is decade after decade - themes that are made explicit in the song’s wonderful video.

Lowlight: Ja Rule – Blood In My Eye

Ja Rule’s career was completely derailed by the superstardom of his longtime antagonist 50 Cent. 50 mocked Ja mercilessly, and Rule’s sales and image took a huge hit as a result. This 2003 album was his attempt at a comeback, but it was derailed by the fact that just about every song was aimed at 50. At the height of Get Rich or Die Tryin’ mania, that was not a subject the public wanted to hear about.

Curiosity: Disturbing tha Peace – Golden Grain

Golden Grain is an unremarkable 2002 compilation album by Ludacris’ DTP imprint. It sold poorly, only had one single (a Ludacris remix, shockingly), and is all but forgotten today. Or would be, if it didn’t mark the first major-label appearances of a rapper then known as Tity Boi, but who would reinvent himself several years later and become a giant star as 2 Chainz.

Big Moves: Turning Japanese (and German)

In 2000, Def Jam opened its first two international companies. Def Jam Germany was the first, and followed shortly after by Def Jam Japan.

The final part of this trilogy will take us through the label’s final decade, featuring the rise of Kanye West, Rihanna, and more.