“Always saw you for what you could've been
Ever since you met me
Like when Chrysler made that one car that looked just like the Bentley”
Listen from the 1:10 mark on Keep the Family Close to hear that particular line. I’m having trouble finding any visual similarities between any product to come from Chrysler and Bentley in the 2000s or 2010s. Take, for instance, the Chrysler 300. Provided that it doesn’t wear an aftermarket mesh grille, it doesn’t hold a candle to any Bentley. Whatever Drake is trying to say, we're dealing with apples and oranges here.
Furthermore, don’t forget that the 300 series from the 1950s introduced the eggcrate grille, the center strake on the hood, dual creases, and side-by-side round headlights. The generation introduced for the 2005 model year is inspired by its predecessors, not a luxobarge with a Flying B badge up front. Then again, the ostracization of the 300 started when the Brits labeled it “the poor man’s Bentley.”
On an ending note, don’t forget that the former chief designer of Bentley designer slammed the Lincoln Continental Concept for looking too much like a Flying Spur. “I would have called it Flying Spur concept and kept the four round lights,” a sarcastic Luc Donckerwolke wrote on his Facebook page in 2015.