His recording of “Long Haired Lover from Liverpool” in 1972 resulted in The Guinness Book of World Records designating him the youngest performer to have a #1 single on the UK Singles Chart. The song was credited to “Little Jimmy Osmond”. In Japan, he had the moniker “Jimmy Boy.”

In 1978, Osmond starred in the feature film The Great Brain. He starred in other acting roles as well, including two episodes of the TV series Fame. He performed on stage and television often with his older siblings.

In 1985, he met Latino impresario Manuel Montoya at A&M Records, and this led to his only Spanish recording, “Siempre Tu”. He toured Latin American markets, including Puerto Rico, Mexico, Venezuela and Chile.

Osmond married Michele Larson on June 7, 1991. They have four children.

He has also featured in musical theater. Like his brother Donny many years earlier, he starred in Joseph and the Amazing Technicolor Dreamcoat. He also starred in Boogie Nights in 2004 at the Grand Theatre, Blackpool. In 2005, Jimmy Osmond’s American Jukebox Show toured the UK in 2005, again to the Grand Theatre in Blackpool. Co-stars of the show included Billy Pearce and Jimmy’s brothers Jay and Wayne. From December 11, 2010 to January 2, 2011, he played Buttons in Cinderella at the White Rock Theatre in Hastings; from December 16, 2011, to January 15, 2012, he played the role of Wishee Washee in Aladdin at Grand Theatre, Swansea; and from December 1, 2017, to January 7, 2018, the role of Abanzar in the pantomime Aladdin at His Majesty’s Theatre in Aberdeen.

He has appeared on several UK TV shows, including the reality TV series I’m a Celebrity… Get Me Out of Here! broadcast by ITV in 2005 (he finished in fourth place), a 2006 appearance on All Star Family Fortunes, a celebrity version of Come Dine with Me, Celebrity Family Fortunes, and Everybody Dance Now. In January 2010, Osmond participated in the British ITV1 celebrity reality television programme Popstar to Operastar. In 2016 Jimmy was a finallist on the UK version of Celebrity Masterchef.

The 2012 Osmonds album I Can’t Get There Without You was performed with Jimmy Osmond on lead vocals; it was the first album to feature Jimmy as lead singer, as older brother Merrill Osmond historically held that role in the band. In live performances, Jimmy often serves as a co-lead singer with Merrill, a role previously held by Donny during the band’s heyday in the early 1970s.

In 2014, Osmond authored a semi-autobiographical children’s picture book, Awesome Possum Family Band.

In 2015, Osmond was awarded an honorary doctorate of arts and humanities by Iowa Wesleyan University. The first Osmond family member to receive that distinction, he delivered the keynote commencement speech on May 9, 2015.

On December 27, 2018, following his performance as Captain Hook in the Birmingham Hippodrome’s staging of the pantomime Peter Pan, Osmond was taken to the hospital where he was diagnosed with having had a stroke. He had previously suffered a stroke in 2004 caused by a since-corrected patent foramen ovale. He spoke publicly for the first time since the stroke in April 2019, stating that he was in good health and was taking a “long-overdue break” from show business for the time being. He has not spoken publicly since then but has continued to operate his businesses including the Andy Williams Performing Arts Center. In a February 2020 interview, Jimmy’s brother Merrill stated that Jimmy continued to recover, still planned on maintaining his business ventures, and that Merrill hoped that Jimmy would eventually return to the group.