Before Nearly Dan, we were a five-piece covers band. We chose to do songs that nobody else was doing. Apart from a fair few Steely Dan songs, we did Chris Rea, Robben Ford, AWB, Was Not Was, Go West, Paul Simon, Sting, etc. It went down really well in the local pubs, but we did a wedding and it bombed.
It all depends on the gigs and venues you are planning to do. But i reckon if you play something well and with obvious conviction, you will always win the majority of the audience over.