Well if your talking both of them two doors then its a tossup for me. I have had a 04 TJR and I wanted more room. I now own a 13JKUR. Lots more room and more comfortable. But not as good off road. YET. I'm gonna go with the JK just cause the 09 has the same trans and a bit more room. You can still put a rubi crawler under the 09, and have Overdrive and a 150 to 1 crawl. The 99 has a 3 speed auto.