Jackson studied at the University of London and then joined repertory theatre in Sheffield, followed by Coventry, Birmingham and Edinburgh. He appeared in several theatre productions early on in his career, including a West End production with Rowan Atkinson and Watford's Palace Theatre's production of The Incident at Tulse Hill. He won the Evening Standard British Film Award for Most Promising Newcomer Actor in 1978.
He continues to work in theatres across the country throughout his career, including a stint as Duke Frederick in Shakespeare's As You Like It in 2000, and most recently in 2004 when he starred as George Pye in Humble Boy at the Northcott Theatre, Exeter.
He appeared in several television series at the beginning of his career starting with one episode of Man About The House in 1973, followed by Anna Karenina, Till Death..., The Legend of Robin Hood, Play For Today, Doctor Who, One Summer and Fairly Secret Army. In 1987 Jackson appeared in the television series Wish Me Luck, with a leading role in all three series between 1987 and 1990. Following the success of this show Jackson appeared in one-off episodes of Maigret, Bugs and Ellington before undertaking a role in the Liverpudlian soap Brookside in 1996-98.
Jackson also made several appearances in the television series Highlander: The Series in 1996-1997. His next television role was in the drama Now You See Her, also starring Amanda Holden. He went on to appear in The White Knight Stratagem, Dalziel and Pascoe and Judge John Deed.
In 1999 Jackson attended the Chronicles 1999 Highlander convention in Birmingham. He took part in a question-and-answers session along with other cast members.
In 2002 Jackson appeared in the television drama Birthday Girl starring Sarah Lancashire. His next television role was as a doctor in the BBC soap/drama Doctors from 2003-04. He has since appeared in Murphy's Law, Casualty, Faith, Dream Team and more recently the ITV drama Mobile which was screened in May 2007.
During October/November 2007 Jackson took part in a reality television show Make Me A Film Star. He was on the judging panel auditioning hopeful actors for a role in a new film which he will co-direct with Phil Middlemiss (also on the panel).
Jackson has been working at Calderstones School in his home city of Liverpool since 2008 as an English teacher, but is now teaching within the Drama department.
In October 2010 he joined the cast of Emmerdale, playing the character Jerry Walsh.
In September 2012, Jackson appeared in Coronation Street as the character Sid Altree.
Jackson's films include Sweeney 2, That Summer!, The Glory Boys, Morons from Outer Space, The Fourth Protocol, There's Only One Jimmy Grimble, and Family Portrait (a 4-minute short film).
Jackson completed filming Pleasure Island in July/August 2013, which has yet to be aired on TV.