Cowell took a few menial jobs—including, according to his brother Tony, working as a runner on Stanley Kubrick's 1980 horror film The Shining—but did not get along well with colleagues and bosses, until his father, who was an executive at EMI Music Publishing, managed to get him a job in the mail room.
Cowell mengambil beberapa pekerjaan kasar-termasuk, menurut saudara laki-lakinya Tony, bekerja sebagai pesuruh dalam film horor tahun 1980 oleh Stanley Kubrick berjudul The Shining—tetapi tidak akur dengan para kolega dan bosnya, sampai ayahnya, yang merupakan seorang eksekutif di EMI Music Publishing, mengaturnya untuk mendapat pekerjaan di ruang surat.