When looking for a hearty laugh or comedic relief after a long day, Bernie Mac is a entertainer who comes to mind for many. The Chicago native began his career performing in the subway and at local nightclubs before winning the Miller Lite Comedy Search competition in 1990. This launched his career and eventually led to his stand-up being seen on “Def Comedy Jam.” Before long, he was journeying across the nation as part of the “Kings of Comedy Tour.” After numerous stand-up specials, movie roles and his own TV sitcom called “The Bernie Mac Show,” the Mac Man has built his legacy in the comedy industry as someone who is authentic and has a no-holds-barred approach when it comes to jokes. Check out eight of his best below.

1. “I ain’t scared of you motherf**ckas!”

Bernie Mac took to the Apollo Theatre stage as he was building his comedic career. Following a comic who had a bad experience, he was faced with the challenge of making one of the toughest audiences in America laugh. With no surprise, he did just that!

As if emerging on the stage in tie-dyed denim pants with his face painted on them wasn’t enough, Mac opened up his performance with the iconic line, “I ain’t scared of you motherf***kas,” which was an instant source of laughter. He kept the audience on the edge of their seats with his jokes — ranging in topic from sex to prisoners — reminding them that he was not scared of them or their ridicule. He even took his set a step further by cueing the DJ for musical accompaniment after various jokes.

2. “Milk and cookies…”

Mac always made it a point to reference his family and their impact on his life. When fans heard his milk and cookies joke, they immediately found humor in a difficult situation: Becoming his nieces’ and nephew’s legal guardian after he took them in due to his sister’s drug abuse. He joked about his experience with all the kids, but especially with his nephew and his behavior.

The milk and cookies joke was based on a story in which Mac asked his nephew where he was going later at night — just before bed. He was soon met with the response: “To get some milk and cookies.” The story gave comedic relief to those who resonated with kids asking for sweets after a specific time and their responses when they don’t get their way. Though many might find this joke controversial today, it still stands as one of Mac’s most famous stand-up bits.

3. “Black funerals be like…”

In this stand-up, Mac dives into racial stereotypes to highlight the difference between funerals held by Black families versus white families. These jokes included viewing the person in the casket, the pastor’s words of encouragement, the length of the services and more. One joke even spoke to how the person in the casket usually looks almost as if they’re holding their breath, and how people make interesting comments.

4. “Put your mama on the phone.”

Mac’s jokes about relationships always hit the funny bone, but this one especially struck a chord for those who have dated Black women and people with children. He told the story of how he decided to stay out later with friends after letting his girl know he’d be back home at midnight. The joke led to him reenacting the conversation in which he communicated that he was getting home later than originally planned. However, in a hilarious twist, the perspective of the conversation changed once Mac revealed he was actually on the phone with her child.

5. “Differences between Black and white people.”

On the renowned Kings of Comedy special, Mac addressed the diverse audience at the show. He then shifted gears and began going through the differences in how the two racial groups respond to things. Whether it be paying bills or preparing to go to a party, many Black people use a different approach than white people do. The audience in the recorded clip could be seen not only agreeing but belly-laughing in the process.

6. “Tell a Black woman you lost your job.”

Some Black women pride themselves on ensuring that their partner can financially provide for their household. In this joke, Mac speaks to the hypothetical experience one may face when telling their partner they’ve lost their job. The joke speaks to the questioning, thought process and aftermath of this situation. The joke stretches even further when Mac shares his experiences of telling his wife bad news and getting annoyed with her for some of her actions.

7. “Women got all the power.”

Arguments in relationships can feel like war sometimes, especially when both sides believe they’re right. Mac depicts the vibrato of the male perspective and the sassiness of the female outlook as the two sides battle over who will “lose” the argument. Mac even touches on the experience of when the woman gets fed up and stops doing her usual chores around the house. In turn, Mac describes this as making the man even more frustrated and forcing him to eventually break down because he misses the woman and craves sex.

8. “Hypothetical versus realistic question.”

Kids always ask the craziest things, right? Bernie Mac told the story of how his nephew asked him the difference between a hypothetical and realistic question. This led to the comic telling the child to ask his mother and sister if they would sleep with the next-door neighbor or the mailman for $150,000. After finding out that both the mother and sister would sleep with those men and more for that amount of money, Mac joked that they should realistically have $300,000 and that the women may need an extra set of eyes on them.