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Two videos were made for Money Don’t Matter 2 Night, the first being directed by Spike Lee, which has footage, shot in black and white, of a family trying to make ends meet. The idea of collaborating on a video with Spike Lee first took root when the director visited the set of Graffiti Bridge. A year later, Prince played him the Diamonds And Pearls album he was working on and asked Lee to pick the song he wanted to direct. The choice fell on Money Don’t Matter 2 Night. He began working on the video just before embarking on the filming of Malcolm X. Prince did not want to appear in the video. Of note, George T. Odom, who plays the main role in Money Don’t Matter 2 Night, also makes an appearance in Malcolm X.
Spike Lee’s storyline of a struggling family in Brooklyn, New York, is interspersed with images of the great depression in the 30s as well as poverty and unemployment in the 80s and 90s. Footage of President George Bush, National Security Advisor Colin Powell, general Norman Schwarzkopf Jr. and (by then) businessman Donald Trump, are also in the footage, as well as images of wealth (a casino, a ball), and shanty-town Soweto, the 1990 war in Iraq and refugees. While in Soweto, South Africa, in late January 1992 for the filming of Malcolm X (which Prince helped finance along with other African-American celebrities), Spike Lee took the opportunity to shoot additional footage for the video. The editing took three weeks, as Spike Lee needed Prince’s approval at every stage. Prince requested that the director alter the ending he had proposed in one of the early cuts, ensuring the video would close on an uplifting note, filled with smiles and positive energy.
Anticipating the intensity of Spike Lee’s vision and wanting to ensure the video could reach prime-time audiences and receive heavy rotation, Warner Bros. requested that an alternative version be created: "That’s one point of view about what the song is about; we wanted to do something that was like a Prince video," said a Warner creative. The second video was directed by Sotera Tschetter and shows Prince and The NPG performing the song in the studio. This video was shot in mid-January 1992, together with footage for the Willing And Able, Call The Law and Daddy Pop videos.
A third video combined the Spike Lee 'political' version with the Sotera Tschetter live band version. This combined version of Money Don’t Matter 2 Night, as well as the Spike Lee version premiered on the same day, 14 April 1992. The Sotera Tschetter performance only video was never released on its own, while both other versions were made available in 2017.
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