Jack first realised his talent whilst as a trainee mechanic he would sing in the garage. He travelled to Germany with the band Serious Women where he first met the members of The Black Romantics his early backing band. He first became popular in the summer of 1995 when he and The Black Romantics took up a residence at Da Club in Dublin. Word of mouth spread and the small venue was soon turning people away. The band played mostly covers of Jacques Brel songs, with one or two of Jack's own, and recorded the album Wax in 1995. Jack eventually split with the Black Romantics and went solo. He has since released a number of solo studio albums. The first of which in 1999 called Metropolis Blue was universally lauded. John Walshe of Hot Press magazine states "Lukeman's voice is powerful and fluid. His range too is impressive, from the deep baritone resonance of 'When The Moon Is High' to the aching falsetto of the magnificent 'Rooftop Lullaby' ... this is a timeless collection of fine songs, beautifully delivered, from an artist as unique as Ireland has ever produced". He released three singles from this album; Georgie Boy, Ode to Ed Wood and Rooftop Lullaby. This was followed in 2001 by the album Universe; Hotpress' John Walshe had the following to say, "... it is as if his older albums were made in black and white and Universe has been recorded in glorious technicolour". Jack also appeared with Nick Cave and writer Patrick McCabe in a series of performances mixing spoken word, poetry reading and song. His powerfully expressive vocals have been compared to such disparate types as David Bowie, Tom Waits, and Frank Sinatra, comparisons that Lukeman himself is unhappy with, preferring to be seen as something unique.