Born in Ottawa, Ontario in 1978, Karl Amani Wailoo is better known to Canadians by his stage name, Saukrates or Bigg Soxx. The Toronto-based rapper is a Canadian hip-hop pioneer, actively on the scene since 1994. He is the co-founder of Capitol Hill Music and the lead artist for the group Big Black Lincoln. Saukrates has been present as a rapper and/or producer on almost every major Canadian hip-hop production over the past 20 years. He released his debut hit “Still Caught Up” in 1994, which earned a nomination for Best Rap Recording at the 1996 Juno Awards. His EP Brick House was released on Slammin’ label the following year in 1997. Warner Bros announced the end of its operations in Canada in 1998, subsequently shutting down Slammin’ label and leaving Saukrates with several recordings and no method of distribution. This obstacle encouraged Saukrates to join forces with his manager, Chase Parsons, to create Capitol Hill Music. Saukrates later released his LP The Underground Tapes in Canada under Capitol Hill Music in 1999, and under The Serious Entertainment label in the United States. “Money or Love”, the third track on The Underground Tapes, earned a Juno Award nomination for Best Rap Recording in 2000.

Taking a break from releasing his own music, Saukrates collaborated and produced hits including “Uh-Huh” for rapper Redman’s Malpractice album (2001), “Heaven” for rapper Nas’ album God’s Son (2002) and “Say I” for an NHL campaign led by PK Subban. Fellow Canadian artist k-os’ “On The Run” was inspired and sampled from Saukrates’ “On the Run”– a collaboration with Nelly Furtado. Saukrates would go on to release his first official debut LP Season One in 2012 under FrostByte Media/eOne Music, an EP titled Amani in 2014, and Season 2 in 2017.

In 2024 Saukrates released a special edition of his debut album The Underground Tapes, featuring 42 tracks with a select few of his classic songs paired with narration from the artist. That same year he dropped Bad Addiction, featuring hit song “Comin Up”. The album encapsulates the pioneers decades long career and further cements his role as a Canadian hip-hop icon.