Ain't It Funny has two videos. The original was filmed in sepia tone and opens with Lopez traveling on a road where she finds a fortune-teller who shows Lopez her future with the cards. A group of female gypsies (one of them played by former Pussycat Dolls member Carmit Bachar) shows up and makes over Lopez so as to make her one of their own. Then Lopez finds a man (played by Mexican soap opera actor Eduardo Verástegui) she could not resist, falling in love with him. In the middle of the video, there is an extended dance sequence, in which she performs a flamenco-influenced routine. Eventually all the people there start dancing together, including Lopez and her lover.
The remix version has two parts which frequently interchange back and forth throughout the song. The first part of the video shows Lopez having a small party in her home with guests including Ja Rule and Ashanti. The second part involves scenes with Lopez and Ja Rule in a white room, Ja Rule in a recording studio in Lopez's home, Lopez sitting in a chair singing bits of the song, and Lopez and Ja Rule singing the parts of the final verse against a gold backdrop.