After the first two series of Auf Wiedersehen, Pet, Nail found himself typecast before creating the detective series Spender, which he co-wrote with Ian La Frenais. The show ran for three series from 1991 to 1993 and also produced a tele-film and a novel. This was followed in 1994 by Crocodile Shoes, which he also created and starred as musician Jed Shepherd.

Although he made a living through acting, his first love was music. He had pop hits with "Ain't No Doubt", written by Charlie Dore, "Crocodile Shoes", and "Love Don't Live Here Anymore". His album Growing Up in Public (East West, 1992) featured Gary Moore, David Gilmour, and George Harrison. Crocodile Shoes (East West, 1994) was based on the BBC television series of the same name, in which he played a mediocre country singer. The album sold nearly one million copies in Great Britain. Big River featured Guitarist Mark Knopfler. Ten Great Songs and an OK Voice (Papillion, 2001) included cover versions of "Walking on the Moon" by The Police, "Something" by the Beatles, and "Overjoyed" by Stevie Wonder. He sang on the film soundtracks for Evita and Still Crazy.

He appeared with Madonna and Antonio Banderas in the film Evita (1996), directed by Alan Parker and adapted from the musical. Two years later, he co-starred in the film Still Crazy.

In 2000 he began work on reviving the Auf Wiedersehen, Pet series, this time for the BBC. It was filmed in 2001 and aired in 2002, with audience figures of over 12 million. Another series saw the brickies holed up in Cuba, and the final two-hour instalment, set in Laos, aired over Christmas 2004 attracting over 7 million viewers.

In 2004, Nail successfully sued News Group Newspapers and Harper Collins Publishers. The lawsuit concerned false and defamatory allegations made two years before in an article in News of the World, a British newspaper, and Nailed, a biography which was the newspaper's source for the claims. He described reading the article as one of the worst experiences of his life. He reportedly received damages of £30,000.

In 2008, Nail created and starred as Phil Parker in Parents of the Band, a 6 x 30 mins series on BBC1, broadcast between November 2008 and January 2009. The series revolves around a group of teenagers who form a band just for their own enjoyment, and their parents, who fully expect them to be nothing less than the next Led Zeppelin. Ratings were disappointing, around the three million mark, and there are presently no plans for a second series.

His work has resulted in five BAFTA nominations (three in total for A.W.P., one for Spender, one for Crocodile Shoes), a Golden Globe nomination (Best Original Song – "Still Crazy"), an Ivor Novello nomination (for "Ain't No Doubt") and numerous other awards and nominations.

Nail came out of retirement to act and sing in The Last Ship, a musical by Sting about the shipbuilders of Newcastle-upon-Tyne, the hometown of both Nail and Sting. Sting grew up in Wallsend, down the street from the shipyards. Nail worked in the shipyards and is the son of a shipyard foreman. The show opened in Chicago. On Broadway, when ticket sales began to drop, Sting replaced Nail to try to save the musical, but it ended after a short run. Nail sang on the Original Broadway Cast Recording and on Sting's album, The Last Ship. He had been due to reprise his role in the UK premiere at Northern Stage on 12 March 2018. The show's Producer Karl Sydow stated: "After protracted negotiations carried out in good faith, we regret to announce the production's offer of employment to Jimmy Nail has been withdrawn. Joe McGann will replace him when the show opens in Newcastle in March. Nail said "I was very much looking forward to appearing in Sting's The Last Ship, particularly here in my home city, Sadly that's not to be." Nail played Parson Nathaniel in War of the Worlds at the Dominion Theatre, London in 2016.