My son isn't nearly as interested in tooth brushing as his sister was at this age, so I kind of get it. But, he becomes more interested when he sees me or big sis do it. He thinks it's fun to watch us and then is slightly more cooperative and more interested in doing his own. I basically just get in there and do it with the brush, but he only has 7 teeth (17 mos) so it's pretty fast. Since you already seem to be having such an issue, what does the dentist say to do? I guess you're already doing the wiping, which probably does help. Are you brushing before or after the nighttime bottle? Do you think he's ready to get rid of that night time bottle? That might help too. They do make batter powered brushes for little kids, you might try that. It makes a funny noise and they are chunkier and easier for him to hold. I have a major issue with plaque and my periodontist said that some people are more prone to plaque and others more prone to cavities...he may be a plaque person like me, which will probably result in fewer (or no) cavities, but the risk of gum disease is higher. I wish I had better advice, but I would press the dentist for more suggestions, and if you're not already, take him to a pediatric dentist. Good luck!