Court records in Los Angeles show Hefner filed for divorce on Friday. He is asking a judge to order him to pay Kimberly Conrad Hefner $US20,000 a month in spousal support.
The records state that's half of the $US40,000 a month that the Playboy founder has been paying her since they separated in 1998.
The couple were married in 1989, the same year Kimberly Hefner was named Playmate of the Year.
She sued Hefner last month, claiming he owes her $4 million under their pre-nuptial agreement and for proceeds from the sale of home she is living in.
Hefner states in court filings that he has paid almost $12 million to his wife and for her home since their separation.