Their tough-guy personas have been dated for a while. In the year of the woke rapper, they finally crashed and burned.

Birdman and Lil Wayne’s media blunders in 2016 have been cringe-worthy, with both rappers storming off mid-interview out of frustration. It’s easy to forget that despite their lack of temperament, they once seemed invincible.

Remember 2006? Fresh off the platinum-selling album, Tha Carter II, Wayne started dominating the mixtape circuit while his mainstream appeal skyrocketed, too. In October 2006 he and Birdman released a collaborative studio album, Like Father, Like Son, which, like most of their prior work, was largely about dope dealing, gang-banging, money and women. It had the same I-don’t-give-a-fuck mantra that helped “Cash Money Records take over the ‘99 into the 2000s.” The album went gold, thanks to bangers like “Stuntin’ Like My Daddy” and “Leather So Soft.” And Birdman had a great solo year too, with features on the remixes for chart-topping singles “We Fly High” and “Make It Rain.”

Their success continued when Weezy dropped the Tha Carter III — the best-selling album of 2008. In 2009, the “father and son” duo signed rising stars Nicki Minaj and Drake to their label, Cash Money Records. The following year, Mr. Carter spent most of his time locked up in prison at Rikers Island, but by the time he got out, his fans had started to move on.

Wayne’s 2011 album Tha Carter IV still went platinum, but the real stars of the label were now Drake and Nicki Minaj. Dwayne Carter was still good for a clever verse on a club banger, but his best days were behind him. As Nicki and Drake extended their sound and drew a bigger following, Wayne and Birdman stayed true to their roots and lost their luster. Mainstream hip-hop culture no longer admired the gangsta rap persona.

Wayne and Birdman’s decline in popularity and shameful media appearances are symptoms of the same problem: They have failed to evolved with the times. J. Cole has become an advocate for criminal justice while still rapping about his romantic goals, like he always did. 50 Cent, once “America’s favorite gangsta,” has fully focused on business and occasionally raps about money, like he always did. Birdman and Lil Wayne still personify “Like Father, Like Son,” like they always did… but that’s it. Wayne tested the waters briefly with “Georgia Bush,” a song that criticized President George W. Bush for his actions post-Hurricane Katrina, but that was over 10 years ago. There’s been little to nothing that takes any kind of stand since.

The duo’s tough guy mentality was celebrated in the ‘90s; it was endearing in 2006; but it’s downright laughable in 2016, when successful rappers need to present more complex and relevant personas.

Here’s a look back at the moment when they fully lost their cool in 2016.

When Birdman asked for “respek” and lost it

The Breakfast Club on New York City’s Power 105.1 is the premiere hip-hop radio show, but it’s also the premiere hip-hop watch dog. The hosts (and in particular, Charlamagne Tha God) will pester any guest, patiently waiting for an artist to slip up before pouncing immediately.

This was the trap Birdman fell into when he entered the studio in April and unleashed a stream of pent-up frustration. The Cash Money Millionaire felt that the radio hosts were slandering his name because of Charlamagne’s past claim that artists were stupid to sign with Birdman’s label since they wouldn’t get paid. Birdman confronted the Breakfast Club and demanded that they show him more “respek” on the show. Unfortunately, it did not end well:

The #1 Stunna walked in the room, folded his arms like a disgruntled toddler, and blessed America with legendary soundbites like “all tree of y’all” and “is y’all finished or is y’all done?” Some of the comments are surreal. Did he really threaten to “pull up on Charlamagne?” Isn’t Birdman almost 50 years old? Why bother challenging a Howard Stern-esque radio personality like Charlamagne? In 2016, stars have to keep cool during interviews. Public figures need to live life like everyone is watching through a Snapchat filter, waiting to press send.

Birdman tried to salvage some credibility and cash in on the joke by releasing a song called “Respek,” but it was too late. The internet had already won. The two-and-a-half minute interview went viral instantly, and the infamous clip is now a part of both hip-hop and meme history.

When Lil Wayne disowned Black Lives Matter

In September, Wayne was a guest on Fox Sports 1’s Undisputed with Skip Bayless and Shannon Sharpe. The co-hosts asked the “Lollipop” singer about race relations in America. He replied that “he’s never experienced racism” and later said he believed “there was no such thing as racism.” Many folks took issue with Mr. Carter’s statements.

White kids loving rap music means there's no such thing as racism. Wow. pic.twitter.com/VFs48nA6pc — Small Freedia (@KidFury) September 13, 2016

A few months later, in November, when Wayne was featured on ABC News’ Nightline, he was asked about his comments from “Skip and Shannon,” and it all went downhill:

It’s inconsistent that Weezy now dismisses racism, since he previously called out former Los Angeles Clippers owner Donald Sterling for his racist remarks. But the bigger issue was how he treated the reporter, Linsey Davis, whom he told not to “come at him with this bullshit,” before storming off and yelling, “I’m not a fucking politician!”

Damn. What happened to the Wayne that held hands with “Miss Katie” Couric during his 60 Minutes interview? He used to thrive in these moments, like a clutch athlete that turned it on when it mattered most.

T.I. said it best: If Lil Wayne didn’t want to share his opinions that day, he should have said “no comment.” Wayne has since apologized for his remarks on Nightline, but it was still a lost opportunity to make a message about race in America resonate with a broader audience, as many of his peers in the industry have helped to do.

In 2016 we saw Killer Mike campaign with Bernie Sanders; Chance the Rapper lead a voting march on election day; and Jeezy share his thoughts on gun control and prison reform on CNN. But rather than watching Wayne take a stand, we watched him melt down.

Like Father, Like Son

It’s easy to feel sorry for the two rappers. Cash Money, the Hot Boyz, Big Tymers, YMCMB and their affiliated groups have blessed our ears with endless hits for almost two decades and helped put the South on the hip-hop map.

But those sorry feelings, like their tough-guy swagger, can only go so far. We’re not asking them to be civil rights leaders; we’re just asking for them not to be jerks. But they can’t even get along with each other right now. The two artists still haven’t resolved their ongoing feud, which means fans might never hear even Tha Carter V. In fact, all we heard this year from Wayne was his album with 2 Chainz ColleGrove and a rather forgettable verse on Chance The Rapper’s Grammy-nominated single, “No Problem.” Sigh.

Bryan “Birdman” Williams and Dwayne “Lil Wayne” Carter should reflect on 2016. If they want to bounce back next year, they might have to do what they’ve avoided for years and get with the times. Their hardcore fans will be rooting for them. But if either one slips up, the internet will be there to hold them accountable.