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I used to do this commute (until 6 weeks ago), from Claremont Ave in Montclair to Madison Ave in Morristown.
At non-peak times you can make it in about 25 minutes. At peak it usually takes closer to 45, sometimes about an hour. The best way to go is 280-80-287 south (unless you live in Upper Montclair, where Route 46 to 80 would be faster). For the most part traffic moves well, with the exception of a delay at the 280-80 LOCAL merge, and in the 80 LOCAL lanes to the 287 split.
For awhile I tried getting off 280 at Eisenhower Parkway. There's often traffic there too, backed up from the light at Eagle Rock Ave. You can get delayed 15 mins or so there on a bad day. But once you're through that light you can sail down to Columbia Turnpike and fly into Florham Park and Morristown.
I'd say that the interstate route is usually better though. The only time I would still go with Eisenhower/Columbia was if I left work in the afternoon between 5 and 6:30. The 80/287 interchange was usually jammed, backing up into Morristown during peak, so the lights on Columbia and Eisenhower were worthwhile. But I usually left work around 7:00 PM when the interstates were usually moving well again.
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