In the first season, the contestants were selected from the first two seasons of Flavor of Love, I Love New York and Rock of Love, and competed in physical and mental challenges in an attempt to win $250,000. Production started in early February 2008, and concluded in March 2008. The show premiered on July 6, 2008 and the casting special aired on July 1. The show is hosted by Craig J. Jackson. The winner was Nicole Alexander better known as "Hoopz".
Season two
In the second season, the contestants were selected from the shows I Love New York, Flavor of Love, Rock of Love, and Real Chance of Love and are competing in physical and mental challenges in an attempt to win $250,000. Production started in late October 2008, and concluded in November 2008. The show premiered on February 2, 2009, with Craig J. Jackson returning as host. The winner was Angela "Myammee" Pitts.
I Love Money 3 would have been a follow-up to the previous seasons of the show. The contestants were to be selected from other VH1 reality shows such as Flavor of Love, Rock of Love, I Love New York, Real Chance of Love, For the Love of Ray J, Daisy of Love, and Megan Wants a Millionaire. Production began in late June 2009 and wrapped early August 2009, with Craig J. Jackson returning to host. Reportedly, I Love Money 3 was set to air in January 2010. In August 2009, VH1 canceled any showings of season three due to castmember Ryan Jenkins's involvement in the murder of Jasmine Fiore, as well as Jenkins's suicide. It had been revealed that Jenkins had been convicted for assault in 2007, but this had not been disclosed to VH1 or 51 Minds. The girls on the show consisted of Flavor of Love'sDeelishis and Buckeey, Rock of Love's Lacey Conner and Marcia "Brazil' Alves, Real Chance of Love's Bubbles, and For the Love of Ray J's Lil Hood, Cashmere, and Cocktail. The boys consisted of I Love New York's Wolf and Pretty, Daisy of Love's Weasel, Fox, Professor, Big Rig and Sinister, and Megan Wants a Millionaire's Joe Pascolla and Ryan Jenkins. As of 2020, the third season remains unreleased. On May 9, 2020, Lil Hood, Weasel, Big Rig, and Joe did one-time tell all on YouTube.
Season four
I Love Money 4 had been announced as the follow-up to I Love Money 3. In April 2010, it was confirmed by VH1 executive vice president Jeff Olde that neither season would air. Despite earlier indicating that the season would not air, it was later reported that the season had been placed into a late night time slot in September 2010, though viewer demand encouraged VH1 to later move the episode premiere to a prime time Wednesday time slot. The contestants were selected from the shows Rock of Love, I Love New York, Real Chance of Love, For the Love of Ray J, Daisy of Love, and Megan Wants a Millionaire. They competed in physical and mental challenges in an attempt to win $250,000. The show premiered on September 16, 2010 with Craig J. Jackson as the host. The winner was Rock of Love's Mindy Hall.
