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Madison on a boy is not that bad. I actually somewhat liked it before the influx of tryndee female Madison, Madisyn, Maddison, etc. If I would have used it though, it would have been a middle name. I also like Monroe, which surprisingly has not caught on with the female crowd as of yet. I would think it would have due to Marilyn Monroe, but whatever.

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Anyway, if you are set on using it in the first name position instead of the middle I would go with:

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Madison Atticus
Madison Clive
Madison Avery
Madison Eli
Madison Fletcher
Madison Henry
Madison Jude
Madison Leander
Madison William
Madison James
Madison Quinn (Although a bit too many surnames)
Madison Robert
Madison Samuel