Eminem has been known to cross boundaries in his career and his guest appearance on SiriusXM radio show “Sway in the Morning” on Thursday, July 23 was no different.

The 42-year-old rapper poked fun at many big names in his freestyle, such as Miley Cyrus, Hillary Clinton, Janet Jackson, Amanda Bynes, Billy Cosby, and Caitlyn Jenner.

According to Us Weekly, the Detroit born rapper's quip at Jenner sparked a lot of controversy.

“This is a true statement, I see the b***** in you, Caitlyn,” he rapped. “I keep the pistol tucked like Bruce Jenner’s d***/ No disrespect though, not at all/ No pun intended, that took a lot of balls.”

The second most controversial lyric was about Cosby's pending rape cases and his treatment of women.

"I’m as off-putting as Bill Cosby is/ Treat women like property," Eminem rapped.

After rapping, the Real Slim Shady, as Eminem is nicknamed, continued to explain that what he says in his raps is not personal.

"It's all in fun. I say s*** to say it," he explained. He then warned that if one of his raps ever was personal, the person would "know it."

Stars such as Mariah Carey, Britney Spears, Jennifer Lopez, and Pamela Anderson have been past victims of Eminem's raps.

Check out the video below to hear the star's full rap.

Image courtesy of Kristin Callahan/ACE/INFphoto.com