Martin Scorsese / Leonardo DiCaprio

When Martin Scorsese teamed up with Leonardo DiCaprio in 2002, it didn’t feel like a one-off casting choice. It felt like the start of a new era. Over two decades, the director and his leading man built one of modern cinema’s defining collaborations, moving from 19th-century gang warfare to Howard Hughes’ Hollywood, Boston crime families, paranoid thrillers, Wall Street excess, and finally the grim American tragedy of Killers of the Flower Moon.

Now Playing Podcast examines every Scorsese/DiCaprio pairing, charting the evolution of both artists along the way. These films are ambitious, indulgent, meticulous, and often explosive. Some won Oscars. Some sparked backlash. All of them carry the weight of two craftsmen operating at full intensity.

The Now Playing Podcast hosts break down the performances, the themes, the excess, and the legacy of a partnership that helped define 21st-century American cinema.