Saukrates in 7 songs

Saukrates is an indisputable hip-hop legend.

Born in Ottawa, he moved to Toronto as a kid and eventually began rapping while in high school. He came up during the '90s golden era of hip-hop, well before Canadian A&Rs were looking for the next big thing in rap. It makes sense then that it was American label Warner Brothers that signed him in December 1996. It was a short-lived stint, however, and he parted ways with Warner in 1998. But label woes didn't keep Saukrates from cementing himself as a crucial figure in rap history. 

His very first single, "Still Caught Up," garnered Saukrates his first Juno nomination in 1996 for best rap recording, a category that was only five years old at the time. Throughout his career, Saukrates has produced for Nas, received a Redman co-sign, and worked with a list of collaborators that include fellow greats Common, Kardinal Offishall, Choclair, K-os, Pharoahe Monch, Xzibit and more. From the onset, Saukrates quickly became known for his unparalleled lyricism and production skills, and his enduring tunes have become an essential part of the hip-hop canon. 

The below tracks are a crash course on the prolific artist, ahead of his headlining performance at the Block Party, presented by CBC Music and Manifesto, on Aug. 11 in Toronto. Tickets are available here. 

Song: "Still Caught Up (Remix)"
Album: N/A (1994)

Saukrates's first single is one he wrote and produced himself, while still a teenager. At 96 beats per minute, "Still Caught Up" is cool and laid back, and the rapper's flow is smooth like butter. It would be an impressive debut for someone 10 years his senior, let alone a teenager, full of a self-assured air and clever lyrics, as he boldly states: "The metaphor is my forte." There's a jazzier original version that features Kool Aid (a young Kardinal Offishall), but it's the mellower version that took off and got airplay on college radio. Almost 30 years later, and "Still Caught Up" has become a cult classic. The track was released the summer before Saukrates's final year of high school, and on it he is coming to terms with the shift in how people treat him as he begins to make a name for himself as an artist. As he told Del Cowie for Noisey: "Everything was changing. I was getting better at my craft and people around me were noticing that, and they were kind of changing around me in the way that they approached me." — Kelsey Adams

Song: "Father Time"
Album: Brick House EP (1997)

With its imposing and repetitive beat, "Father Time" lays the groundwork for a verbal onslaught from Saukrates. The song is four minutes and 11 seconds of him spitting straight fire, with not a moment of filler. Lines like "I gave birth to a novel scene" and Saukrates calling himself "an asset to the rhyming biz" were cocky and prophetic, foreshadowing the influence he would have on the industry. It's a study in expert rhyme scheme, searing delivery and letting the lyrics speak for themselves — and not hiding behind over-the-top production. "Father Time" is a perfect capsule of the sound that defined '90s hip-hop. — KA

Song: "Hate Runs Deep" feat. Marvel
Album: The Underground Tapes (1999)

On one of Saukrates's most searing releases, he samples the Crusaders' "When There's Love Around" for a song that illustrates his prowess as a conscious rapper. Amid the track's dark references to gun violence and prison time, Saukrates manages to deliver an uplifting message that details hip-hop as a way to avoid strife: "But I chose to fight those urges that were foul/ and write prose in spite of foes lurking the prowl," he raps. His vivid bars highlight music as a form of enlightenment, as he showcases his ability to craft a song that's rich with layered storytelling. — Natalie Harmsen

Song: "Pimpin' Life," Big Black Lincoln
Album: Heaven's Caught Fire (2006)

Singing rappers are all the rage nowadays (hello, Drake) but in the early aughts Big Black Lincoln did something revolutionary for Toronto's hip-hop and R&B scenes. Saukrates unveiled another side of himself when he joined Agile, Ro Dolla, Shakari Nyte and T.R.A.C.K.S. to form the R&B group, which were together for a few years in the mid-2000s. Saukrates's ear for melody lent itself well to R&B production, and the same voice that could drop such incisive bars was rich like molasses while singing on a soul track. An irresistible sing-along banger off the group's only album, "Pimpin' Life" was nominated for R&B/soul recording of the year at the 2004 Juno Awards. — KA

Notable collaborations

Song: "On the Run/I Wish I Knew Natalie Portman," Saukrates, k-os and Nelly Furtado 
Album: Season One/Yes! (2013/2009)

This song appears on both Saukrates's 2013 album, Season One ,and k-os's 2009 album, Yes!, under two different names. As the story goes, Saukrates showed k-os the demo track he'd made with Nelly Furtado, and k-os immediately knew he wanted to add a verse to it. It wasn't until six months later, when k-os played it during a show and realized how much the crowd reacted to it, that he knew he wanted the song on his upcoming album. But Saukrates, who also wanted the song on his upcoming album, had already called dibs on the name "On the Run." K-os then randomly chose a name, and "I Wish I Knew Natalie Portman" was born. It's a funny bit of Canadian hip-hop lore that led to an instant classic. All the elements — from the Phantom Planet sample, to their complementary rap styles to Nelly Furtado's haunting line "I can't really make you love me" on the chorus — come together to make one of the best songs of the decade. — KA

Song: "Fades Away," King Reign feat. Saukrates and Drake
Album: Reign Music EP (2009)

Saukrates collaborated with the late King Reign on a number of projects throughout the years, including 2003's "Uptight," but on Reign Music cut "Fades Away," the two Toronto mainstays invited a relative newcomer on the track: Drake. While So Far Gone-era Drake still sounds a bit green, King Reign and Saukrates (who pulls double duty as the producer of the track) stand tall on the piano-laced anthem, name-dropping everyone from James Brown to Kurt Cobain as they discuss greatness and legacy. Saukrates was clear in his goals and intentions in 2009, rapping that he hopes "to put Toronto No. 1 on the Top 10." Little did he know that one of the artists on this track would go on to achieve that very goal several years later. — Melody Lau

Song: "A-Yo," Method Man & Redman feat. Saukrates
Album: Blackout! 2 (2009)

Saukrates's collaborative relationship with Redman started early on, as he produced the track "Uh-Huh" for the American rapper's 2001 Malpractice album and hopped on as a feature for another album cut, "Enjoy da Ride," alongside Method Man and Streetlife. When Redman launched his Gilla House label in the mid-2000s, Saukrates was among the signees. With so many Redman collabs in Sauktrates's catalogue, it's tough to choose one, but this 2009 single with both Method Man & Redman really stands out. On "A-Yo," you're hearing three rappers at the top of their game, taking turns at the mic over a burnished sample of Phyllis Hyman's 1979 track "Magic Mona." "A-Yo" was released as the first single from Method Man & Redman's album Blackout! 2, which was the duo's first collaborative album in eight years (if you include their film soundtrack How High) — and Saukrates's presence on the track was yet another sign of the Canadian rapper's unmatched status in the genre. — Holly Gordon

The Block is counting down to hip-hop's anniversary by airing 50 stories over 50 days that focus on significant artists, events and moments in hip-hop history. The 50 stories will air nationwide each night on The Block on CBC Music until Aug. 11 to coincide with The Block Party.