She was first elected to the Houses of Parliament in the 1987 UK general election as the candidate for the Maidstone constituency. She became the Home Office Minister in Charge of Prisons in John Major's government and in that role she visited every single prison.
During the Conservative leadership election that picked William Hague, she spoke against the former Home Secretary, Michael Howard she served under. She remarked "there is something of the night about him", a comment which was thought to be extremely damaging as he sought election at that time as party leader.
A recent nadir was the own goal which she scored in calling for a zero-tolerance policy of prosecution for users of cannabis in the 2001 Conservative conference. Her speech was well-received by rank-and-file Conservative delegates at the conference. However she alleges that someone connected with Francis Maude[?], promptly contacted journalists to alert them that fellow Conservative cabinet members were prepared to come out and indicate a certain ambivalence towards their own past experiences with this drug.
During the recent 2001 Conservative leadership election[?], after the resignation of William Hague in the wake of the 2001 UK general election[?], she could not find a single Conservative MP to support her as a leadership candidate. In preparation for that contest she began the process of softening her image and raising her political profile, a process that appears to be continuing today despite the selection of Iain Duncan Smith as the new Conservative party leader.
Her fellow Conservative MPs and political opponents have known to be very cruel about her appearance, dubbing her "Doris Karloff" in reference to horror film actor Boris Karloff.
As a strong, forceful and intelligent woman, Ann is one of these unlikely English sex symbols and she has many admirers that talk about how sexy she is. These admirers include Bob Geldof and Eddie Izzard. During the 2001 UK general election the top-selling item at Politico's Bookstore, a London shop devoted to political merchandise, "I Love Ann Widdecombe" underwear was the most popular item sold there.
Ann lives with her elderly mother.