He has partnered with Red River Media to create documentaries on his nephew's custody battle and criticizing "gender ideology.

[15] Later that month, Woolley voiced support for a grand jury investigation into the Oklahoma Department of Human Services.

[16] He was one of three state legislators, alongside Julia Kirt and Dick Lowe, to attend the December 2024 Oklahoma State Board of Education executive session after Attorney General Gentner Drummond issued an attorney general's opinion requiring the board to allow legislator to observe the meeting.

[21][22] Woolley spoke in opposition to wind and solar power in January 2025 alongside Attorney General Gentner Drummond and State Superintendent Ryan Walters.

[23] Woolley identifies as a "former member of the LGBTQ community" and has argued LQBT people should not be allowed to adopt children.

[5] Woolley criticized the Tulsa City Council for allowing a neopagan member of the faerie faith to give the invocation for one of their meetings, describing the prayer as "satanic.