With 15 he begins to write lyrics ("I like to rock, I like to dance, I like pretty girls taking down their pants" MixMag 96), though not with the ambiguity and tricky-ness that showed up later on his albums. At 17, he spent some time in prison because he bought forged £50 notes off of a friend, who grassed Tricky up. In an interview, he says about his experiences in prison: "Prison was really good. I'm never going back." (NME 95).

Eventually he meets DJ Milo and hangs out with a posse called The Wild Bunch, which evolved into Massive Attack. He gets the nickname 'Tricky Kid' from DJ Krust (The Stool Pigeon 2008) and at 18 he becomes a member of the Fresh 4, a rap group built from the Wild Bunch. He also raps on Massive Attack's highly acclaimed debut album 'Blue Lines' which is released in 1992. But as soon as making music turns into a business he doesn't like it anymore. Though Tricky also appears on Massive Attack's next album, 'Protection', he never had the feeling of being a part of the band; never really enjoyed it.

Besides, he already had found his own way of making music. In 1991, before the release of 'Blue Lines', he met Martina Topley-Bird. The story of how they both met may be a myth, but it's a nice one: Martina was sitting on a wall near Tricky's house when he walked by and chatted her up. Some time later she comes to his house, and she mentions to Tricky and Mark Stewart (Bristolian producer and musician now living in Berlin) that she sings. She is only fifteen years old, but her 'honey-coated vox' impresses them and they record a song called 'Aftermath' (though The Face 95 mentions that the first song they recorded together was called "Shoebox").

Tricky shows the song to Massive Attack, but they aren't interested. So in 1993 he decides to press a few hundreds vinyls with that song. He cut it directly off of the tape, so that the song is basically "just bassline and hiss." (NME 94). Finally, this white label gets him a contract with Island Records and he can start to record his first solo album.