 Directed by both Usher and music video director Chris Robinson , " My Boo " clip was filmed in New York City . The storyline of the video is a reflection of the song 's lyrics . The footage starts with Usher in a living room watching a video for " Bad Girl " , a song from Confessions . The " Bad Girl " intro features Usher singing the song in a club setting while <unk> a <unk> @-@ dressed woman . He turns the set off and <unk> down on the <unk> before laying on it with his foot <unk> up . After a moment of silent , nostalgic reflection , he begins to sing the intro of " My Boo " . The video then shows him and Alicia Keys in their separate quarters , preparing to head out , while singing their part of the song . Usher eventually steps out on streets of New York ; likewise , Keys is out in her car . She leaves the car and walks down the street , and the couple meet up in the middle of Times Square , <unk> each other and on the brink of kissing . The music video debuted on MTV 's Total Request Live at number nine on September 16 , 2004 . It remained on the countdown for twenty @-@ seven days , becoming the only Confession video to chart . 
