The worse commute I ever had was about 36 (?) miles one way from South Weymouth northbound, all the way through Boston to Lynn, MA every morning. Ugh! A lot of bad roads back then. It was brutal (ESP in winter). This was back in the early 90s.
I finally had enough and got a nice townhouse in Salem, Ma which cut my commute to about seven miles. It still took me about 30 minutes to get to work. Boston area traffic, in general, was a mess. It probably still is, road, bridge, and tunnel "improvements" completed since notwithstanding.
The second worse commute (pure misery as well) was from Burke, Va to Arlington, Va. It required driving to the train station, parking, after the trip by rail, running a block to catch a bus, followed by a brisk two block walk from the bus stop to the office BLDG. It took about an hour.