1960 was closer in the total popular vote, and had more electoral votes in extremely close states. However, Kennedy had a strong advantage in the electoral college due to the distribution of his votes, and so Nixon would have had to have picked up more votes in more states in order to win - as opposed to Gore only needing a few more hundred votes in Florida. A Kennedy electoral victory with a Nixon popular victory wouldn't have taken much.
green - margin < 1%
yellow - margin < 10,000 votes
gray - margin < 1% and < 10,000 votes
1960:
232 -
181 -
48 -
29 - 47
2000:
242 -
237 -
4 - 55
