The recent tabloid explosion over Sandra Bullock’s husband cheating on her with a heavily tattooed mistress has made us realize that too often celebrities chase after the boys their mothers probably warned them about. Below is a list of famous “bad boy” couples.

Whitney Houston / Bobby Brown

Houston was a bubbly pop star with a girl-next-door personality when she met r&b singer Bobby Brown. After the two hooked up things were never the same for Houston who fell into a downward spiral of drugs and alcohol. The two divorced in 2006, and Whitney relaunched her solo career in 2009.

Britney Spears/Colin Farrell

Although this hook up didn’t last long, Britney and Colin surprised everyone when they stepped out together during a 2003 premiere. Britney, who just broke up with clean, good-natured Justin Timberlake decided to go the opposite route when she snuggled up with the dirty and often intoxicated Colin. Britney made it known to the public that she was not that innocent anymore.

Charlie Sheen / Denise Richards

Charlie Sheen has always been Hollywood’s bad boy, and he has a track record for drugs, prostitution and violence against previous girlfriends. But actress Denise Richards looked past all that when she decided to settle down with Sheen and have two children together. The couple looked happy until their messy 2006 divorce. Richards accused Sheen of domestic violence, prostitution and drugs, aka the same stuff he was always known for. Once a bad boy, always a bad boy.

Evan Rachel Wood / Marilyn Manson

This bizarre couple started dating shortly after Manson got a divorce from his estranged wife Dita von Tesse. The two dated for two years despite the fact that Woods was 19 years his senior. Shortly after their break up, Manson told Spin magazine in an emotional interview that he has “fantasies every day about smashing her skull in with a sledgehammer.” How romantic! The couple got back together shortly after and are currently rumored to be engaged.

Kourtney Kardashian / Scott Disick

The Kardashian sisters seem to all be unlucky in love, but Kourtney has the unlucky advantage of having a baby in the picture. Kourtney’s boyfriend and baby daddy Scott Disick has been described as “the boyfriend from hell.” Disick has been accused of cheating on Kourtney and partying while she stays at home to take care of the baby. The entire Kardashian clan even sat down and had an awkward televised intervention with the deadbeat boyfriend. The two have denied engagement rumors and are currently trying to work things out.