In today’s celebrity-obsessed world, it’s easier than ever to spot your favorite public figures in some of their less-than-shining moments. This is especially true for the intensely personal areas in their lives, like major mistakes when it comes to their parenting choices. For every story about celebrity supermoms like Gwyneth Paltrow or Angelina Jolie, there seems to be two more about famous parents that aren’t quite cutting it. While there are a variety of stories about celebs that just can’t seem to avoid missteps as they raise their children, these 10 have committed parenting sins that have seemed to follow them ever since.

1.     Dina and Michael Lohan – When their daughter Lindsey first appeared on the scene, she was a fresh-faced child with talent to spare and enough charm to set her apart from a field of other young actresses. As she began to get older, however, her substance abuse problems and run-ins with the law were more famous than her films, and it became apparent that many of them stemmed from her turbulent upbringing. In the world of bad celebrity parents, the Lohan parents have created so many maelstroms that it’s difficult to choose just one of their many parenting faux pas over the years.
2.     Alec Baldwin – When tape of Alec Baldwin berating his daughter for missing a scheduled phone call surfaced, the deep enmity and bitterness of Baldwin’s divorce from Kim Basinger and his explosive temper sent shockwaves through the Hollywood gossip community.
3.     Britney Spears – Two of the primary parenting flubs committed by this pop songstress could conceivably be attributed to the incessant hounding of paparazzi, but are still infamous nonetheless. Fleeing photographers with her son on her lap as she drove away or almost dropping him as she fought through the crush of reporters surrounding her before a highly-publicized breakdown that culminated in a loss of custody of her two children made headlines around the world, cementing Britney’s place among parents that have made questionable choices in the public eye.
4.     Courtney Love – Openly admitting to using heroin during her pregnancy with daughter Frances Bean and later losing custody of her due to her regular struggles with maintaining sobriety, Courtney Love isn’t likely to top anyone’s Best Hollywood Parents list.
5.     Michael Jackson – Despite well-known allegations of suffering at the hands of his own tyrannical father, Michael Jackson was, by most accounts, a devoted dad to his children. Still, his excitable nature got the best of him during a trip to Germany, where he dangled his then-infant son Blanket over a balcony in order to give admirers a closer look, despite having the child’s face covered.
6.     Woody Allen – In the annals of Hollywood history, few stories have inspired the level of shock and vague disgust that accompanied the discovery of Woody Allen’s long-running affair with his adopted daughter. Now married parents of two adopted children of their own, Allen and Mia Farrow’s daughter Soon-Yi are still going strong, despite the fact that she entered his life as a daughter.
7.     Eminem – While his devotion to daughter Hailey is well-known, Eminem’s decision to repeatedly release songs about murdering her mother Kim have painted him in a questionable light in terms of parenting.
8.     Kate Moss – Struggling with substance abuse and addiction are enough to cause even the most dedicated parents to make terrible mistakes, but Kate Moss’s insistence on exposing her daughter to infamous British bad boy Pete Doherty and the fact that she missed Lila Grace’s third birthday due to a stint in rehab are parenting mistakes that she’ll likely never live down.
9.     Peaches Geldof – Famous largely for being the daughter of a celebrity herself, Bob Geldof’s daughter Peaches should be familiar with the concept of growing up and parenting in the public eye. That knowledge didn’t stop her from continuing a conversation on her cell phone as her infant son Astala toppled out of his stroller onto the sidewalk. Peaches took to Twitter to blame the incident on the state of London’s sidewalks, insisting that he was strapped in to his stroller and wasn’t hurt. Pictures snapped by photographers tell a different story, however, as little Astala can be clearly seen falling out of his stroller head-first.
10.     Kris Jenner – The matron of the Kardashian/Jenner empire has drawn comparisons to Joe Jackson due to her overbearing insistence on pushing her kids into the spotlight for more money and fame. The moment that lands her the dubious honor of a spot on this list, however, was pressuring her daughter Kim to pose nude for Playboy while cameras of the family reality show were rolling, despite Kim’s reluctance to strip down for the notorious magazine.