A friend of mine went to Japan for vacation about a month ago. Last time we spoke he was on the train headed to Osaka. While he was planning his trip he had asked me to hook him up with a Osaka playlist for when he got there. Of course I included the essential hits by Masaki Ueda, but I also found him some other great artists like Takajin Yashiki, and Masahiro Kuwana. One common theme I find with Osaka music is that they really love the blues. Which makes sense since I'm pretty sure they had a big Blues Rock scene back in the 70s, spearheaded by bands like West Road Blues Band, Funny Company, and Ukadan. Here's some of my favorites, let me know if I should have recommended others.
Osaka Big River Blues (大阪ビッグ・リバー・ブルース) by Ukadan
Sweet Home Osaka by Funny Company
Your Osaka (あんたの大阪 ) by Hako Yamazaki (She's from Oita Prefecture but its still a nice song)
Since coming to Osaka (大阪へ出て来てから) by Junji Ariyama (有山じゅんじ) and Masaki Ueda 上田正樹
おそうじ Obachan by Ukadan