As of the census[10] of 2000, there were 19,100 people, 7,070 households, and 4,835 families residing in the county.

26.20% of all households were made up of individuals, and 11.80% had someone living alone who was 65 years of age or older.

[11] Additionally, there were 7 reported induced abortions performed on women of Jackson County residence in 2017.

Then, from 1988 to 2012, like most of the rural counties in southwestern Wisconsin, it backed the Democratic candidate in each election, and did so by more than an 8% margin each time beginning in 1992.

In 2016, once again like the rest of rural southwestern Wisconsin, Jackson County dramatically swung to the right, shifting from a 15% victory for Democrat Barack Obama in 2012 to a 12% victory for Republican Donald Trump in 2016.

Trump further expanded his margin of victory to over 15% in 2020 and to nearly 20% in 2024, achieving the highest vote share for a Republican in the county since Richard Nixon in his 1972 landslide reelection.