The best way to have your groomsmen smiling is to actually put some thought into the gift, and personalize it. I don’t mean necessarily writing his name on things, but think of purchases that relate with the groomsman’s personal life. Even a clever work item may make a great groomsmen gift if personalized, but again, you can’t just buy a stapler and think you’ve gotten a good gift. I’ll just put it this way, if you know he’s been having issues with faxes, you could get him a nice fax machine, it only takes some insight (but who knows your friends better than you?). Just remember, keep it high quality, and make sure it’s something the groom will regularly use.