John Hughes had a ton of different moments in his career. This is extra impressive given that his career was relatively short. He had his Teen Flick period, followed by his films about love/marriage and then finally his family film phase. It's difficult to pick a best movie for him but Home Alone was definitely his best Family Film and his most profitable film.
It's funny that as a kid I found most of this movie boring except for the ending with all the booby traps. Now as an adult that element is my least favorite part. Now what makes me love the film is the beautiful dramatic pieces, specifically involving the lovely moment shared between Kevin and his creepy neighbor.
Last year I watched this as I sat alone in the house wrapping presents. It was the most lovely Christmas Eve I could have possibly imagined.