He first started to organise club nights, such as Special Branch in London Bridge in 1984 alongside Pete Tong and Gilles Peterson.
[3] Holloway opened the clubnight Trip at the London Astoria in Charing Cross Road at the end of May 1988, and was one of the first legal acid house clubs.
Since cleaning his life up in 1998, Holloway has continued to produce music and is widely known as one of the first DJs in the UK to go digital, many of his Peers mocked him for this, however they soon realised the benefits outweighed the downside and within a few years were doing the same.
Maverick producer Arthur Baker walked into his own club one night, The Elbow Room in Islington and was blown away by what he saw Nicky doing using a piece of software called PCDJ at that time laptop hard drives were too small so he had to carry around a full desktop PC.
In 2008, Holloway started to run classic house club nights under the name of Desert Island Disco however after a few good years decided to stop doing the events as the format was being copied by many other promoters and he simply got bored.