Sean “Diddy” Combs, one of hip-hop’s biggest moguls, has long been a dominant figure in the industry, both as a producer and businessman. Known for his wealth, power, and influence, Diddy has often been seen as someone you don’t cross. But not everyone was intimidated by him. Some rappers stood tall, challenging or even calling him out directly. Here are a few notable artists who never feared Diddy.

1. Tupac Shakur

Arguably the most iconic rapper to have ever stood against Diddy, Tupac’s feud with him was legendary. In the heat of the East Coast vs. West Coast rivalry, Tupac accused Diddy (and Bad Boy Records) of being involved in the 1994 shooting at Quad Studios, which left him injured. Despite Diddy’s immense influence, Tupac never backed down and called out Diddy and Biggie Smalls in his infamous diss track, “Hit ‘Em Up.” He stood his ground until his tragic death in 1996.

2. Suge Knight

The notorious Death Row Records CEO, Suge Knight, never shied away from confrontation, especially with Diddy. During the height of the East Coast-West Coast beef, Suge took multiple jabs at Diddy, even publicly dissing him at the 1995 Source Awards. His fearless approach only fueled the intense rivalry between Bad Boy Records and Death Row, proving that he was never intimidated by Diddy’s stature in the industry.

3. 50 Cent

Curtis “50 Cent” Jackson has never been one to hold his tongue, and Diddy was no exception. 50 has publicly called out Diddy on several occasions, criticizing his business tactics and even mocking him during interviews. He famously questioned Diddy’s credibility and ethics, saying that he was “fake” and calling out his association with former rivals. 50 Cent’s confident, bold demeanor ensured he was never one to back down, even from someone as powerful as Diddy.

4. Jay-Z

Though their relationship has seen ups and downs, Jay-Z is one of the few rappers who has never needed to fear Diddy. Both titans of the industry, Jay-Z and Diddy have often been compared, but Jay’s success with Roc-A-Fella Records and later with Roc Nation allowed him to operate on the same level as Diddy. The mutual respect between the two icons is clear, but it’s also evident that Jay-Z has never needed to fear him or his influence.

5. The LOX

The LOX, a hip-hop group originally signed to Bad Boy Records, are known for their lyrical prowess and strong personalities. After growing frustrated with their contract under Diddy, the group famously went public with their grievances. Styles P and Jadakiss even called out Diddy on radio shows, demanding to be released from their deal. Despite Diddy’s power, The LOX refused to stay silent and stood their ground until they were granted freedom from their contract.

6. Rick Ross

Although Rick Ross and Diddy have collaborated numerous times and have had a relatively friendly relationship, there’s no denying that Ross has carved out his own empire with Maybach Music Group. Ross, much like Jay-Z, has established himself as a major player in the game, proving that while he and Diddy may work together, he’s never been afraid to challenge or stand on equal footing with the mogul.

Conclusion

Diddy may be a force to be reckoned with in the music industry, but these rappers proved that fear wasn’t in their vocabulary. Whether through beef, business clashes, or standing tall as equals, these artists showed that they were never intimidated by the larger-than-life presence of Sean “Diddy” Combs.