1988. What a year. It was Ronald Reagan's final year in the White House. "The Wonder Years" made its debut on TV. Beetlejuice came out in theaters (not to mention the first Naked Gun movie). "Don't Worry Be Happy" was on every radio station. And I was hitting puberty. It was a strange and magical time.
The main reason why I consider this cover the best from February 1988 isn't because McFarlane's name was attached to it (besides, the cover of 300 is without a doubt the superior of the two). It's because it signifies the end of the black costume for Peter Parker, who makes a promise to Mary Jane that he will never wear a black costume again. From 1984 until this issue, Peter would bounce back and forth between his traditional Red and Blue costume and a black suit. Even after he learned the original black suit was an alien, he still went back to wearing black for a couple more years. It was only after his first confrontation with Venom that he vowed to only wear his Red and Blue PJs.
Personally, I always liked the black suit better. But there were plenty more people who were relieved upon learning he wouldn't be wearing a black suit again.
(Note: cover month says "Jun" but the book was released in February).
PAST COMIC COVER FLASHBACKS
As a bonus, here's my runner up for February 1988.