Whoopsie.

Fans who got their hands on Call of Duty: Black Ops II after it hit shelves Tuesday night were the first to discover former CIA director David Petraeus’s fictional promotion on the video game. A scene introduces “Secretary of Defense Petraeus,” a gimmick the game’s developers probably thought was clever when it was originally pitched but now appears egregiously poorly timed since Petraeus resigned from the government amid a scandal with so many tawdry twists and turns that the programming director at Lifetime is probably sitting at her desk giggling, “Tee hee, girl, this is too crazy even for us.”

But it’s not the first time a production company has been burned by a subject’s controversial personal life. Here’s a tour through some of the most embarrassing cameo fails—poorly timed, poorly conceived, or otherwise.

LaToya Jackson in Brüno

Sacha Baron Cohen’s raunchy performance-art comedies Borat and Brüno mine laughs by foisting aggressively odd foreign characters on unsuspecting people and filming their, often hilarious, discomfort. One such victim was LaToya Jackson, who filmed a scene in which she ate sushi off a naked fat man and gamely fielded questions about her brother Michael. But when the King of Pop died just two weeks before Brüno’s release, producers wisely cut the scene. It does, however, show up on the film’s DVD.

Rob Lowe in Oscars Opening

Rob Lowe’s soul-piercing blue eyes lost a bit of their twinkle after the actor participated in a soul-crushing, utterly humiliating opening number at the 1989 Academy Awards, in which he and an actress dressed as Snow White, for some reason, sang a duet of “Proud Mary.” The then 25-year-old recently recalled that he was sure the appearance had just ruined his career. Of course, the debacle couldn’t have come at a worse time for Lowe, as a sex tape showing him having intercourse with two women, one who was just 16 years old, was leaked just two months after. Snow White and the sex tape provided a one-two blow to Lowe’s career that took him more than a decade to recover from.

Charlie Sheen in Being John Malkovich

Charlie Sheen’s wild ride through life on a drug-fueled roller coaster stretches back to the 1990s. In 1998, for example, the actor was hospitalized after a cocaine overdose, turned over to authorities by his father after violating his drug probation, and checked into rehab. So imagine how alarming it was to see the actor pop up less than a year later in a cameo as himself in the trippy indie Being John Malkovich, playing the person talking someone else down from a meltdown.

Mel Gibson in The Hangover II

At the height of Mel Gibson’s spiral down a rabbit hole of ranting lunacy, The Hangover director Todd Phillips booked the actor for a headline-grabbing cameo in the hit comedy’s sequel. Media watchdogs were outraged over the idea of featuring Gibson in what would surely be a box-office smash. (They were right—the film grossed $580 million worldwide.) Apparently some members of the cast and crew weren’t so keen on giving Gibson the cameo so closely timed to his offensive tirades, because Phillips cited that as the very reason when he bagged the Gibson appearance and cast Liam Neeson in the role instead. A scheduling conflict ended with Neeson getting cut from the film as well, and the whole ordeal ended with Nick Cassavetes in the part. The head-spinning chaos is recapped in the clip, thanks to One Minute News.

Lindsay Lohan in MTV VMAs Opening

Everyone loves when celebrities can poke fun at themselves at awards shows. That explains the warm response Lindsay Lohan received during the opening segment of the MTV Movie Awards in 2010. In the skit, she asks host Chelsea Handler if she’s drinking, pointing out that Handler’s fake ankle monitor is going off—alluding to an early incident in which Lohan’s own alcohol monitoring bracelet went off. “Do you think anyone wants to work with a drunk?” Lohan asks. “Take it from me, they don’t.” It was all very tongue-in-cheek and funny…until Lohan’s probation was revoked just 11 days later after she failed a drug test. The starlet’s troubles still haven’t ceased.

President Bush’s Head in Game of Thrones

Seeing the head of anyone familiar impaled on a stick is unsettling—perhaps even more so when that head belongs to the still-living former president of the United States. Dubya unwittingly made a brief, macabre cameo in the first season finale of Game of Thrones, as one of King Joffrey’s beheaded conquests impaled on a pike. The Easter egg wasn’t revealed until the show’s co-creators talked about resorting to using the Bush likeness because they “had to use whatever head we had around” for the scene. Suffice it to say, any cameo of a president’s severed head on a wooden pike is poorly timed, whenever it may be revealed. (Money shot at 1:07 in the clip.)