Rock got the idea for this story from the 1984 Walter Mondale/Geraldine A. Ferraro ticket, in which the democrats thought that since they had no chance of winning against Ronald Reagan/George Bush, they might as well make a historic first so they can win support for the next election. So they ran Ferraro as the first ever woman vice president candidate for their party (and lost).
When the presidential candidates are visiting a school in Florida, the ambulance seen in the background belongs to the Pleasant Valley Volunteer Fire Department of Carroll County, Maryland.
After Mays sees his ex-girlfriend in the restaurant sharing a drink and it starts to rain, the reflection in the windows show that the sky is clear and blue, so it's very unlikely to be raining.