In their heated rivalry, Drake and Kendrick Lamar have consistently taken aim at each other's personal lives, particularly their lifestyles. Drake recently criticized Lamar in one of his tracks, alleging that Lamar is not only shorter but also poorer. Lamar countered with "Euphoria," where he embraces a more modest lifestyle, singing, "Yeah, I'm out the way, yeah, I'm low, okay," and "the island here's remote, okay."

Drake is known for his extravagant lifestyle, epitomized by his sprawling $100 million mansion in Toronto. This 50,000-square-foot estate boasts an indoor basketball court and a lavish great room with 44-foot-high ceilings. Inside, artist Takashi Murakami painted a grand piano, and the furnishings include luxurious materials like ostrich skin and mohair. He also owns a $15 million ranch in Texas and a former $75 million Beverly Hills mansion once belonging to Robbie Williams, which he's attempting to sell.

Lamar's approach to real estate is more reserved. His $16 million Bel Air home, built in 1951, is discreet, revealing only beige siding and framed windows from the driveway. However, Lamar appreciates property investment, having stated in a radio interview that he enjoys purchasing apartments, buildings, and houses. He owns a $523,500 Eastvale home and a $2.65 million Calabasas property. In 2019, he splurged on a $9.7 million mansion in Manhattan Beach, and more recently, he acquired a Brooklyn pied-à-terre in a waterfront condo that also attracted Ed Sheeran.

Drake's "Family Matters" directly targets Lamar's family, highlighting that although Lamar is engaged to his high school sweetheart, with whom he shares two children, they haven't married. Drake taunts Lamar, asking, "Why did you move to New York? Is it 'cause you livin' that bachelor life? Proposed in 2015, but don't wanna make her your actual wife?"

This exchange underscores the intense personal dimensions of their rivalry, which extends beyond lyrics into real estate, relationships, and lifestyle choices.