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.

He has developed and supervised most of the Osmonds' merchandising business, as well as producing hundreds of hours of programming for networks including ABC, PBS, the BBC and the Disney Channel.

In 2005, Jimmy Osmond's American Jukebox Show toured the UK in 2005, again to the Grand Theatre in Blackpool.

In January 2010, Osmond participated in the British ITV1 celebrity reality television programme Popstar to Operastar.

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

The same year, he took over the operations of the Andy Williams Moon River Theatre in Branson, Missouri, where he is now responsible for producing and booking shows.

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.

[11] He has not spoken publicly since then but has continued to operate his businesses including the Andy Williams Performing Arts Center until its 2022 closure.

[15] Source:[16][17] Both sides from same album except where indicated b/w "Silent Night" b/w "Mama'd Know What to Do" b/w "If Santa Were My Daddy" b/w "Give Me a Good Old Mammy Song" b/w "Don't You Remember" b/w "Life Is Just What You Make It" (non-album track) b/w "Uncertain"