- Creator Backlash: A relatively mild example. Lewis said in the foreword of later editions that while Screwtape was one of the easiest things he ever wrote, it was also the least enjoyable. As he put it, it caused a kind of moral cramp, forcing himself into a demonic mindset. He also resented it for not being something he felt he wasn't skilled enough to write - Screwtape's advice balanced by angelic advice from Heaven. For these reasons, he never wrote a sequel, though he did write a toast (a scathing criticism of the American educational system at the time and its resulting Tall Poppy Syndrome) in Screwtape's voice.
- Evil Is Cool: Subverting this is pretty much the whole point. Not only is Screwtape himself a stuck-up member of Hell's middle management and a cranky Jerkass with no sense of humor, but he gives tips to Wormwood on how to minimize how much The Patient can enjoy sinning.
And anyway, why should the creature be happy?!