What Indian Head Penny is worth the most?

Among regular issues, the clear winner is any 1877 cent. These retail for around $3,000.

However, there are some mint error Indian cents that sell for even more. An 1873 with the Word Liberty appearing twice, kind of like a ghost image, sells for as much as $11,000. But the absolute top is an 1888 coin struck from a die that was re-used from 1887. There's a faint 7 visible underneath the last 8, and these can retail in the range of $15,000 to $20,000.