Snapchat's parent company, Snap Inc., had its big day last week. It filed the paperwork for its long-awaited IPO.

The ephemerally friendly social media app is going public in hopes of raising $3 billion. While a valuation for the whole company has yet to be mentioned, Snap's IPO is expected to be one of the biggest in tech history.

Snap's road to success didn't come without a few potholes. During this blindingly bright spot in Snapchat's history, we thought it was justthe time to take a look back at the moments Snapchat wishes would disappear.

Here are Snapchat's 10 most embarrassing stumbles:

1. The frat boy emails

The most famous of all Snapchat blunders was when co-founder and CEO Evan Spiegel's raunchy, sexist emails from his undergraduate career at Stanford were leaked and subsequently published by Gawkerin 2014.

Their contents painted Spiegel as a reckless frat boy with a penchant for joking about peeing on women. He also REALLY didn't want anyone to touch the stripper pole.

Spiegel later apologized for the emails, saying that they "in no way reflect who I am today or my views towards women."

2. When Snapchat released "black face" and "yellow face" lenses

Snapchat debuted lenses — those beloved digital masks that transform your face — in 2015. Since then, it has rolled out not one, but twooptions that were perceived as racist.

Last year, Snapchat thought it had found a clever way to celebrate April 20, an internationally recognized weed smoking holiday, by giving its users the opportunity to transform into Bob Marley.

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The lens added dreadlocks, a knit hat in Rastafarian colors, changed the shape of the eyes and noses of users and darkened their skin color.

Snapchat said the filter was built in partnership with the Bob Marley estate, but it still offended because it felt too reminiscent of blackface. It also implied that Bob Marley's career was solely about weed and failed to highlight his musical contributions.

The second lens, released several months later in August, gave users slanted eyes, exaggerated teeth and puffy cheeks — a come-to-life version of racist Asian stereotypes.

Snapchat disabled the filter and offered an explanation: It was meant to be a tribute to anime characters. But for Snapchat users who had experienced racism, the filter instead represented a hurtful stereotype taken to an extreme.

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The decision to build the two filters led to speculations that Snapchat might have a larger problem with diversity.

The company hasn't released demographic data on its employees, breaking custom with other major tech firms like Facebook and Google that regularly release stats on their workforce.

3. That time Spiegel lied to Forbes

In a splashy 2014 cover story for Forbes, Spiegel alleged that he had confidentially brushed off Mark Zuckerberg when the Facebook founder emailed him asking for a meeting.

Spiegel said he told Zuckerberg to come meet him in Los Angeles, where Snapchat is based. In reality, Zuckerberg politely offered to head there himself.

After Business Insideraggregated the back and forth and labeled Spiegel as "arrogant," the Snapchat co-founder tweeted a screenshot of the correspondence with Zuckerberg (the tweet has since between deleted) to try and derail the arrogant narrative.

The screenshot showed that Spiegel's actual conversation with the Facebook founder was filled with more smiley faces than you would have expected, given what he said to Forbes.

The magazine was was not happy, and publishedthe transcript of exactly what Spiegel told their reporter J.J. Colao on tape.

In effect, Spiegel caught himself in his own lie. The app boy wonder played himself.

4. Reggie Brown's grueling court battle

In 2013, Snapchat's third founder, Reggie Brown sued the company's other two other co-founders, Spiegel and Bobby Murphy.

Brown said they had taken his original idea, refused to give him credit or compensate him for his contributions, and ultimately pushed him out of the company unfairly.

The lawsuit alleged that Brown was part of the founding team and helped put together Snapchat's first patent applications. Most crucially, it argued that Murphy came up with the idea that the messages should disappear.

You know, the whole novel part of Snapchat.

When a settlement was first announced in 2014, the financial details of the suit weren't made public, but the press release from Snapchat did admit that Brown was indeed a cofounder and that the original idea was his.

In Snapchat's IPO filing last week, we learned the juicy details of the dispute: Spiegel and Murphy paid Brown a whopping $157.5 million to settle the case.

Disappearing pictures is a multi-million dollar idea indeed.

5. When Snapchat lost its high-profile COO

In 2015 Snapchat lost its COO and former Instagram executive Emily White.

Sources told Recodeat the time that Spiegel let White go because he wanted more control over the company.

That makes sense—Snapchat's IPO paperwork shows that even when the company is officially public, he and co-founder Bobby Murphy will still retain full control.

White was the third top executive to leave the company in the span of two months.

6. That time Evan Spiegel said diversity is "not the best use of time"

In 2015 Spiegel backed himself into making a series of cringe-worthy statements about diversity at Recode's second-annual Code Conference.

When Recode's Walt Mossberg asked Spiegel why he thought diversity was a problem in tech, the billionaire founder deflected, answering that "diversity is a challenge everywhere." Mossberg pushed on, but Spiegel refused to budge. "I think I'm saying that diversity is a challenge everywhere, including tech. And that's kind of that."

The audience grew uncomfortably hushed, and then Spiegel dropped an odd answer that caused them to become dead silent.

Mossberg asked again if Spiegel thought there was a problem specifically with diversity in tech (spoiler: there is) and the former frat boy blurted "There are so many things that feed into diversity and equality that unpacking them on the stage is probably not the best use of time." Awk.

7. When the stars of early Snapchat sued

Elizabeth and Sarah Turner filed a lawsuit against the disappearing messages app in 2014, alleging that Snapchat had taken advantage of them by failing to provide compensation for a modeling gig.

The suit said that Spiegel misused the images he had taken of the Turner sisters, effectively turning them into the "face" of Snapchat without their permission.

Spiegel had apparently told the Turners that the images were for a "class project," instead of, you know, what would become a multibillion dollar company.

The worst part is that the Turner sisters claim one of the photos was cropped and edited by Spiegel or someone else at Snapchat to look like Elizabeth was pulling Sarah's bathing suit top off.

Snapchat's IPO paperwork shows that the case is still currently ongoing.

“The matter is currently in active discovery. We believe that the lawsuit is without merit and intend to continue to vigorously defend ourselves in this matter. Based on the preliminary nature of the proceedings in this case, the outcome of this legal proceeding remains uncertain,” Snapchat writes.

8. That time millions of accounts were leaked

Over New Year's in 2014, hackers stole and published the user names and private phone numbers belonging to over 4 million Snapchat profiles.

The worst part? It looked like Snapchat blatantly ignored the security vulnerability that allowed for the hack to happen in the first pace.

A week before the hack took place, Gibson Security published exactly how to exploit the security flaw because they were "sick of" Snapchat ignoring their warnings for months.

The icing on the cake was Spiegel's decision to refrain from apologizing for the hack.

In an interview with NBC's Carson Daly, Spiegel said "I believe at the time we thought we had done enough. But I think in a business like this and a business that is moving so quickly, if you spend your time looking backwards, you're just going to kill yourself."

Snapchat the company — but not Spiegel personally — eventually issued a very short apology.

Oops.

9. The Sony hack emails

Leaked emails from the 2014 Sony Pictures hack included correspondence between Spiegel and Sony Pictures CEO Michael Lynton, who now sits on Snapchat's board of directors.

The emailed painted a picture of Spiegel's ambitions for then less than 3-year-old company.

The Snapchat CEO was reportedly mortified that the info had gone public, and wrote that he felt like he was "going to cry" in a memo distributed to Snapchat employees and later posted on Twitter (the tweet has since been deleted).

While there wasn't anything particularly scandalous in the exchanges, they made Snapchat's overall business strategy uncomfortably public. Yikes.

10. When Snapchat admitted it gave snaps to the police

In a 2013 blog post, Snapchat admitted it had handed over unopened snaps to law enforcement at least a handful of times.

Until a snap is opened, it's stored on Google's cloud computing service, which Snapchat uses. When the intended recipient opens it, it's deleted.

But if the snap is never read, law enforcement can request to see it via search warrant. When that happens, Snapchat revealed, they're happy to comply.

To be fair, at the time over 350 million snaps were sent on the platform daily, so an incredibly small amount were ever requested and subsequently viewed by law enforcement.

Still, the incident showed that Snapchat, like other big tech players like Facebook and Google, share data with government authorities semi-regularly.

UPDATE: Feb 8, 2017, 6:18 p.m. ESTThis article has been updated to reflect the correct spelling of Walt Mossberg's name. It's Mossberg, not Mossburg.