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Short of creating custom audio and a custom playlist, is there a way/app that will act as a virtual DJ for a wedding including things like introducing the guests who are going to speak, daddy/daughter dance, chicken dance, etc? I could do everything in a playlist but if someone has already done this then it's all the better.

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    Instead of a DJ, I spent months making a playlist. Sure enough, when it was time for the groom and mother dance, my iPod started acting up. While I had tested shortly before working fine, but when it was time, it wouldn't play DRM'd songs. It was annoying and embarrassing. Just hire a DJ, or have a friend manage it all for you. But don't try to automate it.
    – jmlumpkin
    Commented Nov 29, 2011 at 13:25

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it's your wedding. Do you really want to have an IT solution to manage during a wedding. If it fails, what are you going to do? I don't doubt that the app does some cool stuff but you want the least amount of things that can possibly go wrong at a wedding. Sorry for the non-IT answer.

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Since it's a wedding, the only recommendation I can make is to hire a professional DJ that can work the crowd. Predefined playlists might be fine for ambience music during dinner etc, but they'll never get the real party started. You need some interaction with the crowd if you ever want to get them on that dance floor. Also don't assume timing of a wedding party goes exactly as planned when you think of automatically announcing speakers etc, it just doesn't work out that way.

There is quite some DJing software available however. A popular choice is djay (also available for iPad). But a good set-up goes further than that. You can have a look at this page for a more extensive guide on DJing on the Mac.

But again, please go for an experienced DJ. It's worth it. I'm sure he has his own set-up, wether it be digital or analogue.

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