The 5 Pettiest Celebrity Moments of All Time
Media training is not particularly uncommon for celebrities. They are often instructed on what to say and how to say it to maximize their public perception. That doesn’t mean celebrities are above being petty ever so often, though. We’ve collected five examples of celebrities going rogue and acting out. Do you think there are petty celebrity moments that beat these?
Julia Roberts made a homemade t-shirt to shade her husband’s ex
The start of Julia Roberts and Danny Moder’s romance felt a little complicated. Moder was married to makeup artist Vera Steimberg when he met Roberts on the set of The Mexican in 2000, and Roberts was in a long-term relationship with actor Benjamin Bratt at the same time. While the pair insist that they didn’t leave their partners for each other, Roberts made it pretty clear how she felt about Moder’s ex during the early days of their relationship.
In an oddly petty moment, Roberts was photographed, nonchalantly sipping on a beverage, while wearing a homemade t-shirt that read “A Low Vera.” Given the timeframe, her relationship status, and Moder’s ongoing divorce, the shirt was clearly a reference to Steimberg. Fans were troubled by the move, considering it rather immature, all things considered.
Patti Lupone sued Andrew Lloyd Webber, then built the Andrew Lloyd Webber Memorial Swimming Pool with the settlement
In the early 1990s, stage actor Patti LuPone was cast as Norma Desmond in Sunset Boulevard. She appeared in the London run of the show on the condition that she would move to the Broadway version at a later date. She was later replaced and never made it to the Broadway show. The move prompted LuPone to sue composer Andrew Lloyd Webber for breach of contract. The courts sided with LuPone and ordered Webber to pay the actor $1 million.
LuPone decided to sink the settlement into a little home improvement project. She took the settlement and built a pool in her Connecticut backyard. That’s not the petty part. The petty part was the pool’s name. LuPone dubbed the swimming pool the Andrew Lloyd Webber Memorial Pool. Webber is very much alive. The pool still stands, and LuPone’s decision remains one of the pettiest celebrity moves of all time.
Lana del Rey put up a billboard for her new album in her ex’s hometown
Lana Del Rey didn’t take her breakup with Sean Larkin well. Del Rey was so deeply bothered by the split that she decided to be as petty as possible when releasing new music. Del Rey funded exactly one billboard to promote her album, Did You Know That There’s a Tunnel Under Ocean Blvd. According to People, she dropped the billboard in Larson’s hometown of Tulsa to get back at him.
What makes the move even more outrageous is how short the relationship actually was. Del Rey and Larkin dated for about six months before splitting in 2020. Del Ray’s album dropped in 2022, releasing it on her ex’s birthday. In 2023, she continued to shade the now-married Larkin with song lyrics.
Demi Lovato told papparazzi to “ask Taylor” about Selena Gomez
Demi Lovato and Selena Gomez grew up together on different sets and were inseparable until they reached their late teens. They were actually best friends once upon a time. When Selena Gomez started to get close to Taylor Swift, Lovato didn’t take it well. In one very petty moment, Lovato told the papparazzi they should “ask Taylor” when they asked her how Selena Gomez was doing.
It’s all water under the bridge now. While Lovato and Gomez are no longer close, there doesn’t seem to be bad blood either. Gomez gushed about Lovato and her talent during a 2025 podcast appearance, and Lovato insisted she was thrilled that Gomez was happy during an appearance on Watch What Happens Live with Andy Cohen. Lovato and Swift seem to be on decent terms, too.
Drake used Kim Kardashian’s voice to shade Kanye West in one of his songs
Drake has been the victim of petty celebrity moments, but he’s also pulled a few punches, too. The music artist’s longstanding feud is no secret, but did you know he shaded his nemesis by sampling Kim Kardashian’s voice on one of his songs?
In 2023, Drake released the single “Search & Rescue,” which samples a clip of Kim Kardashian talking about her decision to divorce Kanye West. In the song, Kardashian is heard telling her mother, Kris Jenner, “I didn’t come this far to come this far and not be happy…” While the song was a hit, West’s fans were outraged at Drake’s decision to throw a subtle jab, by way of Kardashian, at the rapper. Later rumors that Drake and Kim Kardashian were actually dating made the move seem even more petty.
