I don't actually like playing drums with headphones. I have 3 types of headphones, one VERY isolating (Senn HD280pro), one semi isolating (Senn HD201), and one open (Senn HD414). My problem with the 280's is that I can't hear the drums. With the 201's, the drums come through, but only slightly more. The 414's are OK, but like most open-air headphones, I can't hear the bass that well.
I prefer playing along with speakers instead. This is because I can "feel" the vibrations of the bass, and hear the sound my drums are producing. The former is important because 1) the bass gives me the root of the chord changes so I know where I am in the song, and 2) it allows me to keep the rhythm section tight. The latter is equally important because I obviously need to know what sounds I am producing, and am very sensitive about it. It helps that I have an "old-skool" stereo with 3-way speakers.