But as much as the show may have limited the storytelling opportunities with this decision, they’ve been able give audiences a glimpse into a tragic yet inspiring historical figure. As fun as it is to watch him push all the right buttons on his stand-up sets on the show, it has a lot more impact now that we know exactly what the cost of his truth-to-power style of comedy will be. As Kirby himself put it in an interview with Parade:
We also kind of feel duty-bound because Lenny is a historical figure and a lot of us know about his own life, we’re sort of addressing that in ways, too, and kind of setting some of the magic and diving in a little closer to find the cracks. That’s kind of exciting for me.
Although Lenny Bruce was having run-ins with the law from the very first season, it’s only in the season 4 finale, “How Do You Get to Carnegie Hall?” that his addiction problems are shown on screen, when Midge finds a small bag of unspecified drugs in his bathroom. She’s concerned, but Lenny assures her that “all is well,” and she reluctantly lets it go.