I'll be honest, it's taken me a while to get "into" doing a lot of Hollywood's early films, including silents and the Golden Age stuff, mainly because I felt inadequately knowledgeable about them and was gonna sound like a dimwit if I ever wrote about them. If you'd asked me twenty years ago to watch a silent movie I'd have laughed right in your face, but now I'm more mature and open to their… history, so to speak, I'm inclined to watch with an open mind on subject and quality. Not every silent movie I've seen has been awesome (Hitchcock's early silent film output had about 1 great one to 3 or 4 shitty ones) but there are some diamonds there if you know where to look.

I feel inadequate suggesting one to start with, mainly because I've really only started my own journey with them myself, but one that absolutely surprised me with it's visual brilliance and stark visceral-ness was Hitchcock's "The Lodger", which comes as close to replicating what I think a good Jack The Ripper movie might be like. That one legit surprised me with how good it was. If you watch it and can't find that entertaining, then just stick to more modern stuff because I don't think they get better than The Lodger. I have a review somewhere on the site you can check out, but it's worth a look for the beginner silent film watcher.