I'm thinking half an hour is too short. Our show is an hour and a half long but I don't wanna bore my audience if they don't like her. Nonetheless:
Originally Posted by zeroryouko
There are a lot of ways you could play this, depending on what you're going for. Not knowing the intended audience, it's hard to choose.
Consider for example:
Should every song be written, composed, and sung by Ringo herself?
Or, are songs written/composed by her band mates OK?
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Well, one of my co-hosts is insisting that we play OSCA, so I'm okay with stuff she didn't write. Also while I didn't really like It Was You very much, I think it's seriously cool that she worked with Burt Bacharach and that might get a listener's attention.
I can't say I'm a fan of Utaite Myouri enough to have the final say on that. What do you think?
Do you want mostly accessible tracks, that casual listeners might enjoy?
Or, do you prefer to go into more depth, with tracks that might take even a seasoned listener a while to appreciate?
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I'm inclined to lean towards the former, although we play some pretty weird stuff on our show so I'm not averse to that at all. Ideally some of both.
Do you want to showcase Ringo's versatility, with tracks in a variety of different styles?
Or, do you want to present the idea that Ringo has a certain unique style or theme, and play tracks that exemplify this?
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Personally, I think her versatility is a huge part of what makes her special, so I was gonna head in that direction. Something more poppy, something weirder, something more jazzy, etc.
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Do you want to stick to "Western-sounding" tracks, or include tracks that are more "Japanese"?
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Both.
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Do you want to include studio tracks only, or are live tracks on the table as well?
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Live tracks are absolutely on the table. I'd really like to play the ZCS version of Yattsuke Shigoto.
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Singing in English: yea, or nay?
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I had HF Kuki, JL005, Karada, Mayakashi Yasaotoko etc. on my list of possible inclusions, so I'm going to go with yea.
Originally Posted by tsukigimehime
Agree with above.
I think it would be hella cool to start with Marunouchi Sadistic and end on Expo ver.
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I didn't really think about doing something like that with different arrangements, could be a neat idea.
Tadashii machi
Ishiki
Bokoku jouchou
Chichinpuipui
Konya wa karasawagi/kamisama, hotokesama
Kurumaya-san/bokoku jouchou
Ariamaru tomi
tsugou no ii karada
remote controller
mellow
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Bolded the ones I have on my list.
... If it were me, I would honestly just spin favorite tracks and hope that people got more interested than put off 
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Sure, but I thought it'd be fun to get you guys involved. Your collective knowledge is a lot better than mine.