He has an individual brother and three half-brothers; younger brother Nicholas Cowell, half-brother Kim Cowell, half-brother Tony Cowell together with half-brother Michael Cowell. Michael is a oldest, followed by John, Tony, Simon and Nicholas respectively. 
Cowell attended Radlett Preparatory School and the independent Dover College as did his brother, but left after taking GCE O levels. He passed in British Language and Literature and then attended Windsor Technical Higher education where he gained an additional GCE in Sociology.  At age 17, he dated product Paula Hamilton.  Cowell took a few menial jobs‚????including, according to Tony, working as a jogger on Stanley Kubrick's The Shining‚????but didn't get along well using colleagues and bosses, until his father who was executive at the recording giant EMI Music Creating, managed to get him their employment in the mail room.
Cowell's father's connections in the beginning got him rehired as the assistant to an A&R person. From there onwards, Simon worked his way up and at last got promoted to a music publishing position but left in the early 1980s to form E&S Music together with his boss at EMI, Ellis Rich (later Chairman in the Performing Right Society). The company had a lot of hit records at one point with five singles in the uk top 40. The offices were in a converted gentleman's washroom inside NCP car park on Brewer Street in London's Soho district. Cowell left by mutual agreement a long time later. He worked for Iain Burton, manager involving choreographer Arlene Phillips, co-founder with dance group Hot Chat and of nascent independent record label Fanfare Records. Cowell worked with Burton with regard to eight years at Fanfare the place he achieved his first real success in the music industry, becoming an associate and building Fanfare to a highly successful 'indie' pop label. Fanfare had numerous top hits with various take artists and particularly Sinitta, selling more than 500, 000 copies involving her debut single "So Macho", and more than 500, 000 copies of her album Rondo Veneziano. Following in 1984, Cowell and Burton met up with Pete Waterman for the very first time.
Mike Stock, Matt Aitken and Pete Waterman produced the songwriting and record producing trio known as Stock Aitken Waterman. Stock Aitken Waterman helped Fanfare in the second half of the 1980s producing several hit singles for Sinitta together with licensing The Hit Factory SAW Compilation Albums to help Fanfare. Next in 1989, Fanfare's parent, Public Company, found again in difficulties, forcing Fanfare in the hands of BMG, and an in-debt Cowell was forced to move back in with their parents. Later that year, he became an A&R coordinator for BMG.
Subsequently, Cowell signed up several acts to S-Records that became successful, including Curiosity Killed the Cat, Sonia, A few, Westlife, Robson & Jerome, and Ultimate Kaos. He also released various novelty recordings featuring the likes of Teletubbies, wrestlers of WWE Zig and Zag along with the Mighty Morphin Power Rangers, that were huge successes.  Within 2002, Cowell set in place another label, Syco Popular music, which later became component of Columbia Records and Sony BMG Music Entertainment. "simon Cowell", "simon Cowell"