The longest was Lexington to Florence, KY for about 3 months. Wasn't that bad, was usually early morning or late at night so I didn't run into many issues...biggest problem was getting out of Lex quickly.
The worst was from Northern KY, Southern portion of county to Mason, OH near King's Island. It was like 40 miles but with decent traffic it was just over an hour. If there was a wreck it was horrendous. The worst part was I would have to leave 30 minutes before I theoretically needed to just to factor in an incident so 90% of the time I'd get to work 30 minutes early. Fortunately it wasn't a daily drive as I was in sales and didn't have to report to the office daily. I was constantly in my car though. Back in those days it wasn't uncommon for me to drive 100-150 miles a day all within one given market.