Jay-Z’s recent entrance in to the overly crowded streaming music wars is a reminder that celebrities sometimes invest in questionable things. It was entertaining watching Leonardo DiCaprio’s version of a manic Jordan Belfort – The Wolf of Wall Street – crawling in the squalor of wealthy excess knowing full well “nice guy” Leo probably makes smarter investments in real life.

In fact, we have a tendency to distance celebrities from the millionaires they play onscreen from the millionaires they are in real life. To us, they’re well put-together individuals, more concerned with mansions and high-end fashion; their money keenly managed by teams of high profile investment advisers no, doubt.

But like kids in a candy store, celebrities have been known to make silly investments. So to make you feel better about that sub-par startup you might have considered throwing your money behind, we’re going to pick on a few celebrities. Here are seven ridiculous investments in the tech sector by clueless celebs.

Justin Timberlake still hasn’t given up on Myspace

In June 2011 the pop artist-turned-actor and Specific Media paid US$35 million for the ailing social media network. Unfortunately, it’s yet to see a significant lift in membership numbers. Our advice: just because you played a social media startup investor, doesn’t mean you know what’s up. Quit trying to make MySpace happen, Justin.

Tom Hanks makes a typewriter app

File under: there’s no reason why it should succeed. Tom Hanks found some app store success after his useless but well-designed typewriter app for iPad – Hanx Writer – ranked first in productivity apps and overall in August. Why? Beats us. “Hanx Writer is just my little gift to the future Luddite hipsters of the world,” the Castaway actor told USA Today. Apparently he’s still waiting for the rest of us to get the joke.

Bieber fans don’t really want Shots of Me

You think investing in a selfie app would be a no-brainer for teen idol Justin Bieber. Unfortunately, despite his legions of Beliebers, the singer’s US$1.1 million investment in Shots of Me still failed to knock Instagram off its throne as the go to for self-adoration.

Sean “Diddy” Combs and Ashton Kutcher’s tiny failure to launch

You think the hip hop artist who introduced the world to the Notorious B.I.G. and Steve Jobs wannabe, er… got-to-be Ashton Kutcher would know a thing or two about hyping a crowd. But the pair’s hand in a US$1.5 million investment in video communicating and messaging platform Tinychat failed to ignite much interest. And with better-known competitors like Chatroulette and SnapChat it looks destined to nosedive in an already saturated market.

Turntable.fm failure another reason for Kanye not to smile

It’s the failure of virtual DJ Turntable.fm – which Kanye West was part of a US$7 million round investment in – that remind us why the hip-hop superstar superstar doesn’t like to smile. The platform, which launched in the summer of 2011 boasting 140,000 new users in its first month, slowly fizzled out. It was revolutionary at the time, playing nice by paying labels and artists for every stream. Unfortunately, playing nice doesn’t get you far does it Yeezy?

Ryan Seacrest familiarizes himself with the other kind of judges

For Ryan Seacrest, typing out emails while surrounded by swarms of elbowing teenagers probably leads to more than a few false autocorrects. That could be why he co-founded Typo – a mobile keyboard for smartphones – investing US$1 million of his own funds into it. Unfortunately, the screaming crowds must have drowned out Blackberry’s claims Typo was a “blatant infringement against BlackBerry’s iconic keyboard.” Now the entrepreneur can add contempt charges to his achievements.

Neil Young’s hearing seems to be going with PonoPlayer

Well, that didn’t take long. Neil Young’s US$400 PonoPlayer – a portable music player touting high quality audio – was hardly in display cases before audiophiles turned against it with cries of snake oil. When contrasted with an iPhone, the Neil Young founded and championed brand’s product failed to illicit more than shrugs. Keep on searching for a startup of gold, Neil.

Jay-Z shows he can invest in streaming music too

Since Dr. Dre became the first billionaire rapper last year following Apple’s acquisition of Beats, his premium headphone brand and streaming music service, we can only imagine things got weird between him and his friends. Does Dre pick up all the checks at dinner now? Is it cool to borrow his pure gold Bic pen if you need to write something down quickly? Jay-Z is trying to fix that with his recent acquisition of Aspiro, the Swedish company that runs the streaming service WiMP, for $56M.