Celebrities who've been in gangs

A lot of celebrities like to make themselves seem like gangsters, whether it means posing with guns, wearing certain colors, or just dropping certain references in their musical lyrics or public appearances. However, not many stars can actually claim to have been in gangs in real life — and those who can often may not be forthcoming about it, because, well, there's that whole "crime" aspect of organized crime. Beyond the bright colors, street cred, and cash, there's often a dark underbelly of drugs, violence, and fierce rivalries, and gang allegiances have been rumored to be behind the untimely death of some stars.

Whether it's Snoop Dogg promising to make America Crip again, Cardi B pledging allegiance to Bloods and avoiding the color blue, Frank Sinatra rubbing elbows with Gambinos, or Lil' Wayne lashing out over his gang loyalty in a televised interview, these stars have all been linked to (or openly part of) gangs.

Chris Brown seems 'bool' with it

Chris Brown has been close with several members of the Fruit Piru Bloods throughout his career, likely much to the chagrin of his attorney and probation officers. In July 2014, Breezy posted several references to the gang on Instagram and during his shows, reported TMZ. Those nods included using "bool" instead of "cool" in an Instagram caption and throwing up gang signs and shouting them out onstage.

However, some insiders claimed that while Brown openly affiliates himself with the Bloods, he's not a fully initiated member. However, sources told TMZ that the Bloods are okay with Brown claiming them because the troubled singer supposedly hired several members to work for him in various capacities, with some even living with him in his Los Angeles home. Sources close to the gang also claim Breezy has given their Compton neighborhood an "economic boost" and often comes to hang out with them, even shooting a music video in the area. The gang particularly appreciated his kind gesture of donating 1,000 pairs of sneakers to underprivileged children in Compton.

Danny Trejo's 'crazy' past

Before Danny Trejo was a tough guy onscreen, he was a self-described crazy guy in gangs and in and out of prison. He talked about his time as a gangbanger with The Huffington Post in 2013: "We had a lot of pistols, and you don't really want to mess with somebody who's got a lot of pistols … You've got to remember: People aren't scared of tough guys. People are scared of crazy people."

He told The Guardian that at one point, he was facing multiple potential death penalty sentences. "I went to the hole looking at three gas-chamber offenses," Trejo said. "After the Cinco de Mayo riots at San Quentin, in 1968, they said I threw a rock and hit the lieutenant in the head, but you know what? I did hit him in the head with a rock. But I wasn't throwing it at him, I was throwing it at a group of guys and he happened to be hit. So we all had gas-chamber offenses, and we were taken to the hole and I remember saying: 'God, if you're there, everything will turn out the way it's supposed to. If you're not, I'm f**ked.'"

Trejo isn't impressed by celebrities who try to claim gang status. He cracked to The Huffington Post, "All the rappers become very famous and then try to get street credit. They get caught playing with machine guns and it's like wait a minute … You're no longer a thug, you're a businessman."

Nick Cannon escaped to Nickelodeon

Nick Cannon was embroiled in the Bloods gang growing up, though he didn't necessarily want to be. He told Vlad TV, "I wouldn't say I joined a gang … I grew up in a neighborhood in Southeast San Diego — this public assistance area called Bay Vista. And that was kinda the thing … Actually, if anything I was always trying to get away from it. Of course, during the early '90s when it was glorified I definitely was wearing my Dickies and certain colors and the Chucks."

He added, "It was a Blood set, but it was one of those things where that's the area that I grew up in. I mean, even if you think of Southeast San Diego, the majority of the people from down there are from different Blood sets … I lost a lot of friends to senseless gang violence. A lot of people still locked up right now. So I always try to downplay it and be like that cat that was allowed to get away from it … Yo man, once Nickelodeon called I locked in. I forgot about all of that stuff."

The Game is an understanding member of the Red Nation

The Game grew up in Compton, Calif., and peppers his lyrics with references to the Bloods, even dropping an entire LP, The R.E.D. Album, dedicated to the lifestyle. In fact, the lead single from the project, "Red Nation" (featuring Lil' Wayne) was actually banned from MTV and BET in 2011 before it ever premiered, allegedly because it was too gang-affiliated. 

At the time, The Game said in a statement (via XXL), "No love is lost for BET and MTV. I know they have standards for all ages watching the networks. I didn't want to change the artistic integrity of the music video, and with the amount of people watching videos online, I know all my fans will still be able to find it."

He also talked about the ban with Dub magazine (via XXL): "I didn't fight it. I have kids and understand why the networks didn't want to show it … They may have banned it, but it still blew up on the Internet."

Lil Wayne, Young Thug, Birdman, and a big mess

Lil' Wayne, Young Thug, and Birdman are rumored to be affiliated with the Bloods gang — and in a bizarre twist, that gang was accused of trying to murder Lil' Wayne. 

Rolling Stone obtained court documents that described Lil' Wayne, Young Thug, and Birdman as members of the gang and alleged that Jimmy Carlton Winfrey — who served as Young Thug's tour manager — was a high-ranking Blood who shot at Lil' Wayne's tour bus in April 2015. The indictment cited an alleged threat Winfrey made in Young Thug's "Halftime" video, in which Winfrey can be seen holding a weapon similar to that used in the shooting. The legal docs also claimed that Young Thug threatened Lil' Wayne on Instagram leading up to the incident.

For his part, Lil' Wayne frequently references the Bloods gang. When asked in a November 2016 Nightline interview if he supported the Black Lives Matter movement, Weezy pointed to his red bandana and said, "I don't feel connected to a damn thing that ain't got nothin' to do with me … I'm connected to this motherf**king flag right f**king here. I'm connected. I'm a gangbanger, I'm connected."

Was Frank Sinatra serenading mob bosses?

Frank Sinatra's exact mob ties are unclear, but he was friendly with several Italian organized crime family members. According to the Daily Mail, many of the clubs Sinatra performed in early in his career were owned by the mob, and it seems ol' blue eyes family was at the very least acquainted with certain mobsters, including Meyer Lansky, Bugsy Siegel, Dutch Schultz, and Lucky Luciano, who were reportedly friends with his parents when he was growing up in Hoboken, N.J.

Sinatra's close friend Phil Silvers' wife told the Daily Mail that Sinatra was oddly fascinated with Siegel's violent tendencies. "[Sinatra and Silver] would brag about Bugsy, what he'd done and how many people he'd killed," she said. "Sometimes they'd argue about whether Bugsy preferred to shoot his victims or simply chop them up with axes … [I never forgot] the awe Frank had in his voice when he talked about him. He wanted to emulate Bugsy."

Sinatra was called to testify in court when he was suspected of potentially running millions of dollars between Lucky Luciano and Al Capone's bodyguards, the Fischettis. The Sultan of Swoon admitted to meeting with Luciano, but insisted he was just saying hello at an event and denied any further involvement, though he'd allegedly continued to rub elbows with organized criminals for the rest of his heyday.

D.L. Hughley is not proud of his past

Comedian D.L. Hughley was a member of the Bloods growing up. He told Vlad TV, "As a young boy you're looking for acceptance any way you can get it. Although I'm not proud of what happened, I'm not proud of my experiences, I learned a lot from them that I think is invaluable for me in terms of how I see the world." He admitted, "I thought they were the clearest, [most] honest, bravest human being I'd ever met … I think they were some of the best human beings I'd ever met," explaining that he interpreted a lot of the gang's activities to be "illegal, but not immoral."

His stance changed somewhat when one of his own cousins, a member of a rival gang, was killed by Bloods. "That was difficult because … he was one of my favorite cousins, and when he died they wouldn't let me go to the funeral … Bloods had killed my cousin." 

He then left the Bloods to avoid any more violence. "I knew I didn't have it in me to take human life. It just seemed brutal to me."

Ice-T created a 'fake gang'

Rapper and actor Ice-T was affiliated with the Crips growing up in the Crenshaw neighborhood of Los Angeles. He told The AV Club, "You're either with them or without them. You kind of get indoctrinated into that lifestyle, like I say on one of my records, whether you're in a gang or not, you know what color to wear. You don't want to wear the wrong color just to cause a problem … Gangs are real. They fight to the death."

Though he was never actually an indoctrinated Crip, Ice-T says he pretended he was. "We actually created a fake gang. We told people we were part of the Hillside Crips. We had them thinking there was hundreds of us. We connected together …  it kind of kept people off of us," he said. "By 10th grade, you start to know people from the different neighborhoods. I've always had a very cool, charismatic personality, and as long as you meet the shot-callers and the troublemakers and they like you, you ain't got no problems."

Snoop Dogg wants to 'make America Crip again'

Snoop Dogg was long affiliated with Los Angeles' Crips gang, and he makes no secret of his loyalty in his music. In October 2017, he dropped an eight-song LP, Make America Crip Again, the cover of which was largely comprised of an image of the gang's signature blue bandanas. In the title track, Snoop lashes out at President Donald Trump, spitting, "The president said he wants to make America great again, f**kt hat s**t, we're going to make America Crip again."

Still, Snoop doesn't necessarily endorse the violence associated with gang life. He told Vibe in a statement about the album title, "What I mean by that is — in my lifetime, that's when young black men in impoverished areas organized to help their communities and to take care of their own because society basically left them for dead. A lot of people glorify the gang banging and violence but forget that in the beginning, the Crips' main and sole purpose was to be the reflection of the Black Panthers. They looked after kids, provided after school activities, fed them and stepped in as role models and father figures."

Robert De Niro aka 'Bobby Milk'

Before starring as mobsters in Goodfellas (1990), Casino (1995), and The Irishman (2019), Robert De Niro was an actual gangster when he was just 14 years old. De Niro went by the nickname "Bobby Milk" because "he was pale and strange as milk," reported Vanity Fair. He joined a street gang in New York's Little Italy.

Martin Scorsese, who directed De Niro in his infamous mobster roles, first met the method actor during De Niro's days as a gangster. Scorsese told Vanity Fair that when he ran into De Niro at a Christmas party in 1971, "I said to him, 'Hey! Didn't you use to hang around Hester Street?' Bobby didn't answer, just stared at me — he does not look at you, he considers you — so I stared back. Then I remembered: 'It was Kenmare Street — the Kenmare gang.' And Bobby goes, 'Heh heh!' I hadn't seen him in fourteen years … We were both guys who'd grown up on the street."

Dipset seems partial to the color red

New York City rap group The Diplomats, commonly called Dipset, have all been long-rumored to be affiliated with the red bandana-waving Bloods.

Dipset member Jim Jones has been the most forthcoming about his connection, telling Vice in 2006, "I've been affiliated with the Blood gang since I was a teenager. And for y'all that's not familiar with the court of law, being a member of a gang, being a Blood is not a crime, you know what I mean? That is not a crime to be a gang member … it's what you do as a gang member, that's when you get conspiracy charges and racketeering and all that. Me being who I was, I just came up in a hood that was a Blood neighborhood."

However, he added, "I don't care where you gangbang at, it's people dying, it's young youth dying all that time. Gangs are killing each other and at the end of the day, it's f**king up our hood regardless of where we're coming from, that's what people really need to know."

Member Juelz Santana also admitted to Dipset having Blood ties. "I been gang-affiliated since day one. Everybody knows that, everybody know we got a heavy affiliation with the Bloods since day one," he told MTV News. "…People around me happen to be around more Bloods than anything else, so they assume that's what I'm doing. But I know Crips too. I know Latin Kings."

Suge Knight may be the godfather of gangsta rap

The Los Angeles Police Department claims Death Row Records founder Suge Knight was affiliated with the Mob Piru Bloods — and that his loyalty to the gang led to the murder of rapper Tupac Shakur.

An LAPD source told People that Mob Piru was in a "deadly rivalry" with Compton Crips that led to Shakur's shooting. "Mob Piru was built off of Death Row [Records]," the source said. "They had been around for a while, but Suge put them on the map and they started making money and became big." The source added that when Shakur signed with Death Row, he "immediately [became] enemies with the Crips."

The insider told People that the day Shakur was shot, he got into a scuffle with Crip member Orlando Anderson. "It was simple retaliation: you mess with one of ours, we will mess with one of yours. If Orlando had never been jumped in the hotel, they never would have killed Tupac that night …Immediately after Tupac was shot [in Las Vegas], the next day there were murders all the way back in LA because the Compton Mob Piru (which Suge was a part of) knew that the Southside Compton Crips were involved."

James Caan is chummy with the Colombo crime family

Actor James Caan starred as Sonny Corleone in The Godfather (1972) and has an actual real-life tie to the Mob: He's close friends with Colombo crime family bigwig Andrew Russo.

Caan told the New York Post in 2011, "My friendship with Andrew Russo dates back over 35 years, and I've only known him to be as good a friend as anyone could be to me and my family." 

Caan also wrote a letter to the court for a bail hearing for Russo that said, "Our two families are intertwined. My son Scott is his godson … [Russo] has always been the first to call when any member of my family has been ill or troubled, and always looked after me like a brother … I'd be willing to put up anything of personal value that the court would accept [for bail]. I would not hesitate a moment to fly in and be present if the court should so request. In short, there's nothing I wouldn't do to see this man where he belongs and where he is needed the most — with his family."

Tekashi 6ix9ine is a colorful fellow

Rapper Tekashi 6ix9ine considers himself affiliated with the Bloods. In his video for "Gummo," he hangs out with a large group rocking red bandannas. However, rumors that he switched from Crip loyalty to Blood loyalty have haunted the rainbow-haired MC, and his video for "Kooda" shows he's certainly not unfriendly with the blue crew. However, he has denied actually being a Crip, telling The Breakfast Club (via Revolt), "There's this crew called Scum Gang from Flatbush. I used to run with them, but nobody can say who I'm Crip under. Like who was I Crip under?"

6ix9ine has faced a slew of trouble throughout his brief career due to his gang affiliations and criminal history. In February 2018, TMZ reported that he was jumped at LAX. The site also reported that the Tango Orejon gang in Texas attempted to ban him from performing in San Antonio, Texas, but failed to block the performance — one of their members was reportedly arrested for threatening 6ix9ine.

Cardi B wears 'bloody shoes'

Cardi B was a Blood before hitting it big.

"When I was 16 years old, I used to hang out with a lot of … Bloods," she told GQ in April 2018. "Sometimes it's almost like a fraternity, a sorority … and sometimes I see people that's in the same gang kill each other. So sometimes there is no loyalty. Sometimes you gotta do certain things to get higher, to get higher and higher. You're doing all of that and you not making money off of it. That's why I don't talk about it much. Because I wouldn't want a young person, a young girl, to think it's okay to join it."

She added, "People always be like, 'Oh, Cardi never used to rep it when she wasn't making music.' … When I do interviews, I don't talk about it, because I will lose my endorsements. But since the cat is out of the bag, that's how I feel … Why would you join a gang?"

Her Blood affiliation almost got her into hot water ahead of a Los Angeles concert in February 2018, when she dissed rival gang the Crips. According to TMZ, Crip members began to threaten her on Instagram. Still, it makes the "Bodak Yellow" lyric "These is red bottoms / These is bloody shoes" a lot more interesting.

Josh Brolin was a delinquent surfer

Josh Brolin is great at playing bad guys on screen, from Thanos in Avengers: Infinity War to a dirty detective in American Gangster. Perhaps some of his villainous skill comes from his past as a member of the Cito Rats surfer gang.

Brolin told The Guardian that when he was a teenager in the gang, he'd steal radios from cars for drug money and was usually in some kind of trouble — and some of that trouble could have killed him. "I tried heroin," he admitted. "I never got into it and I never died from it, which is a good thing. I've had 19 friends who died. Most of those guys I grew up with, they're all dead now."

He also told Men's Journal (via Radar Online) that he'd served time behind bars before he could even legally buy a beer. He was reportedly involved in a brawl at age 19 that eventually turned into a physical altercation with police who'd arrived on the scene.

"To this day, I have no idea what the fight was about. I woke up in jail," Brolin said. "The police were very angry with me … They kicked my a** really well. I was looking at a long time in prison. So, basically, I put everything I had — everything I had earned from a TV series I did — into lawyers. I did a bit of jail time. Not much, but a little bit."