People who don't love musical theater just don't know what they are missing. But some guys, especially the rougher-tougher types, won't give the art form a chance. It's important to reach out to those guys with the material that might catch their attention. So think about what sorts of things the guy is interested in, and then try to find shows that match the subject matter. Remember, this isn't about you and your interests. It's about him, and getting him excited about this art form.
Find out what's available in your area, by checking your local newspaper's entertainment guides. Look for shows that not just might match the interests of the guy but definitely will be of high interest. This might take some patience. But it will be better to choose wisely the first time, rather than having a so-so experience and then trying to get the man to go back.
Once you've picked the perfect show, start dropping hints about going to it. Maybe strike up a conversation about the general subject matter. Or mention that you saw something about it in the newspaper. Get a dialogue going. Stoke that interest. Plan a night out. Suggest going to the guy's favorite restaurant, and then drop the suggestion that afterward, you go see this show.
Gauge his reaction. If he seems interested and open, take him up on it. If he seems like he's just appeasing you this time, consider looking for another show at another time and trying again. Remember, you really want this to be a great experience, so he wants more.
If the date is set, take care of all of the details yourself. Make this as easy as possible for him. Order the tickets. Get a gift card for the restaurant, so it doesn't feel like a big dinner bill is part of the package. Drive. Pay the parking. Keep his focus on the show.
Dress up for the night. Leave the cellphones behind. Make the evening feel special. Go early to dinner. Have a drink or two. Make sure there aren't any schedule conflicts or childcare concerns and that he doesn't have to be up early in the morning.
Stop by the concession booth and pick up a little memento from the evening. That way whenever you see it around the house, you can remind the guy what fun the show was.
When he has a good time, keep talking to him about it, and start planning the next one. This time, with his buy-in, you really can start honing in on his interests.