Shortly after his birth, his father Oliver and mother Muriel split up, forcing his mother to raise him as a single parent. Until he was 13, the two of them moved constantly throughout different neighborhoods in Toronto where Cale would initially become exposed to hip hop culture. He began rapping at age 9 and as a teenager started performing amateur rhymes under the pseudonym "Cale the Lyricist". Inspired by the 'golden era' of hip hop, he has highlighted Wu-Tang Clan and KRS-One on numerous occasions. Growing up, Sampson was also influenced by non hip hop artists such as Bob Dylan and Johnny Cash.
In 2002 he became a member of the group Rhythmicru. This collective was part of a new wave of underground acts that emerged during the late 1990s/early 2000s, and in 2003 they released their debut LP 'Open Canvas'. The album received wide critical acclaim, led by Sampson's groundbreaking solo track ‘The Facts of War' which Jason Richards of NOW Magazine called "the most incendiary anti-war track ever created" (Jan. 22nd, 2003 ). This song exposed Rhythmicru's music to a whole new market and helped add the label of "outspoken political hip hop artist" to Sampson's reputation.
Appealing to both underground and mainstream audiences, his subject matter is very diverse. Prominent themes in Cale's music include references to his status within the Canadian hip hop community, his relationship with his mother (a notable song being 'It's Not Time'), a public disdain for George Bush, and a recurring focus on promoting a positive message. He also addresses topics ranging from the potentially negative impacts of genetic research to several no-nonsense ruminations about his personal life. Punch lines and vivid imagery are also trademarks of Cale Sampson's rhyming style.
Despite the serious themes in many of his songs, his work also has its fair share of light and humorous subject matter, including 'Women & Alcohol' and 'Distractions Part 2'. In the latter, Sampson insults celebrities and makes critical comments about reality TV, Scientology, and Donald Trump, among others. A number of his songs also lack the typical verse/chorus structure in favor of showcasing significantly extended rhyme patterns. Chart Magazine touched on this during its live review of the 2005 North by Northeast Music Festival – "Cale Sampson was the most explosive – he busted through an entire track using only words that began with C,A,L and E. Now that's talent" ( June 10th, 2005 ).
He has opened for such acts as Guru from Gang Starr, Pete Rock, Non Phixion, and Atmosphere, among others. He has traveled across North America as part of the legendary Vans Warped Tour. He has also performed all around Asia, most notably when his group headlined the 2007 Spring Scream Music Festival in Taiwan.
The year 2008 marked a significant turning point in Sampson's career. In order to whet Cale's listener's appetites, he will release his long awaited debut solo album aptly titled ‘Cale Sampson'. Collaborators include acclaimed Canadian hip hop producers Classified and DJ Kemo of The Rascalz. The album is expected to be one of the most creative and original Canadian rap releases to date, revealing Sampson as one of the game's true bright spots.