(28 June 2000 - 14 February 2006) (divorced)
Perelman met his fourth wife, actress Ellen Barkin, at a Vanity Fair Oscar after-party in 1999. After slightly more than a year of courtship, the two married in June 2000. All accounts indicate their five-year marriage was a stormy one. Much of the friction arose due to Barkin's acting career and her attendant travel schedule. Perelman filed and obtained a divorce in early 2006. The press soundly mocked Perelman for his actions, the speed and timing of which suggested his real motivation was to avoid a clause in his prenuptial that would raise the amount in alimony he owed Barkin if he waited a few days longer. Depending on the source used, Barkin's yearly alimony ranges from $2 million to $3 million and the total payout ranged from $20 million to $65 million In late 2007, the pair exchanged lawsuits. Part of the divorce settlement required Perelman to invest several million dollars in a film production company Barkin and her brother George (an aspiring screenwriter) had started. Perelman made only one of the payments, claiming that there was no evidence the two were actually producing films. Barkin sued for her money while Perelman counter-sued, alleging Barkin and her brother had looted the film company for themselves.