Fours with a Five Wing
A Five wing often adds intellectual muscle to Fours' feeling-intensive, hypersensitive modus operandi, bringing complexity and depth to their lives and to their creativity. The blending of a piercing intellect with emotional intensity helps them become confident in their individualistic skin and more capable of utilizing their insights in productive ways. They burn with creative fervor and often produce successful works of art. They also try to think their way out of their emotional doldrums.
On the other hand, Fours with a Five wing may become more conservative, self-contained, subdued, private, and analytical. When they take on more of the analytical bent of Five energy, they are often drawn to solitary professions such as a researcher, using their intellect to be a scientist, or using their fascination with feelings as a psychologist or therapist.
Many Fours with a Five wing are geniuses in their creative field. According to The Enneagram Movie and Video Guide, prime examples include Diane Arbus, Marlon Brando, Eric Clapton, Kurt Cobain, Bob Dylan, Sylvia Plath, Arthur Rimbaud, Edgar Allan Poe, and Virginia Woolf. All combined exceptional intelligence with an artistic soul, which resulted in original works of art that captured the world's attention. Unfortunately, many of them fell prey to a Four's susceptibility to a deeply pathological depression that led to suicide.
On the negative side, Fours with a Five wing can become even more introspective and solitary. Sometimes Five energy leads to quirky or idiosyncratic behavior, or a feeling of being so different they feel alienated. This could result in further social withdrawal and longer periods of isolation that, unfortunately, bolster Fours' proclivity for unproductive brooding or feeling sorry for themselves. Fours with a heavy Five wing who spend too much time alone can get lost in nonproductive rumination, depression, and morbidity.

