Glad I'm not alone. I got a Silca Pista pump for 5 bucks at St. Vinny's, and replaced the rubber seal in the head. The old seal was noticeably reamed out. It's pretty futzy. I'll try some of the suggestions given here. It would be nice to get a classic old pump working.

Note in edit: I probably wasn't pushing it on far enough. Thanks for the tip. Also, a bit of spit helps it slide on further.