At the age of 12, McCutcheon obtained her first acting role and was paid £350 to appear in an American television commercial for the drink Kool-Aid, which was followed by modelling assignments and bit parts in TV shows. She was given the part of Mandy in the TV series Bluebirds (1989) alongside Barbara Windsor, and played Susan, Jane's sister (played by Denise van Outen), in the Anthony Newly directed production of Stop the World – I Want to Get Off, at the Churchill Theatre in Bromley, London, later transferred to the West End Lyric Theatre in Shaftesbury Avenue. This was followed by two guest appearances on the ITV police drama The Bill in 1991 and 1992. McCutcheon also appeared in the music video for the song "Caribbean Blue" by Irish singer Enya. By the time she was 15, she was part of an all-girl group, Milan, with two fellow pupils, and landed a record contract with Polydor and a gig touring as the warm-up act for the British boyband, East 17. Milan were reasonably successful. Three of their singles: "Is It Love You're After", "Affectionately Mine" and "Lead Me On", charted in the top ten of the dance charts, with the latter also making it to the top 100 of the UK Singles Chart. However, they were not successful enough to make a living and disbanded.