Over at Cigar Aficionado's excellent Cigar Cinema, Jack Bettridge and Dave Savona share some excellent advice on pairing cigars with Irish whiskey.  The cigar is one of their top 25 cigars, and is nicely priced at $6.25, but the whiskeys are all rather high-end.  I am not an expert with the Irish whiskeys, but can say that in the past I've enjoyed Tullamore Dew quite a bit.

You can watch the video by following this link.  Make sure to check out Mr. Bettridge's excellent herringbone tweed jacket.