Controversial personalities are fun to delineate and there are few who are as controversial as Bill Maher. His chart below:
Bill’s Sun (ego) is in Aquarius and Moon (emotion, instinct) is in Taurus. Aquarians tend to do dig in their heels when it comes to their ideas and Taureans tend to dig in their heels over everything. As both signs are fixed, these are indicators that Bill can be a bit stubborn about things and this is evidenced by the many public arguments Bill has had over the years. There isn’t much evidence of Bill “walking back” a comment or changing his mind once it’s made.
Aside from this general observation, Bill’s Aquarian-Taurus nature can reflect a personality that struggles with itself. While his Aquarian life force is much more tolerant of progressive concepts or ideas, his Taurean nature doesn’t necessarily embrace over-complication. Specifically, this friction can be best seen in the juxtaposition of Bill’s Libertarian demeanor existing within the multitude Liberal causes he supports and spurs a motivation to bring advanced concepts and ideals down to earth with common sense explanations.
Bill’s Libra Ascendant adds a unique twist to the “big three” line-up as it adds an element of charm to how he operates and this has probably assisted with being in front of the public as both a comedian and a host. His Ascendant ruler, Venus, is positioned within the 5th house of creativity, making a sextile aspect to the Moon (10th ruler) and a trine aspect to his Midheaven. These relationships make a strong statement that his creative talent will have a direct impact on his career and the exalted status of each ruler (Venus in Pisces, Moon in Taurus) confirms the high potential for success.
Bill’s grand square (Neptune-Moon-Uranus-Sun) is the center-piece of the chart as it contains the Sun-Moon combination. Grand square configurations are known for their willpower and concentrated focus, so the stubbornness noted earlier is underscored here. Specifically, its self-contained nature can become highly impenetrable, making the individual resistant to outside pressures. This is why Bill has been able to withstand some of the fierce responses to his comments and opinions. Also, this configuration is angular so its characteristics will be highly active and visible.
The individual components of this combination aren’t too difficult to analyse. The core elements of Bill’s personality (Sun-ego, Moon-emotion/instincts) are coming to terms with the archetypes of rebellion, irreverence, spirituality, drugs, and left-leaning socialism as represented by the outer planets of Uranus and Neptune. Again, their interplay with the two strongest pieces of Bill’s personality will ensure that the larger, transpersonal archetypal concepts they represent will become synonymous with his very essence and is evidenced by Bill’s gradual evolution towards left leaning political positions and his irreverent nature or ability to go against the status-quo.
The next major configuration is Bill’s t-square involving an opposition between Venus-Jupiter-Pluto with Mars-Pluto squaring each side. With a t-square configuration, the apex planet(s) in square aspect to both sides of the opposition becomes the focal point of manifestation, heavily motivated to resolve the issues going back and forth between the opposing polarities.
One of the unspoken truths of comedy is the pervasive sense of nihilism it inadvertently promotes. Its method is to address that which is precious, important, sensitive or sacred from a perspective that diminishes it to the level of profane or ridiculous with laughter being the result of the unseen realization. But taken to its extreme, everything can be ridiculed because “nothing is sacred”. Many comedians hold back when performing because if they shared their raw, honest thoughts it would be considered inappropriate, too negative or “too soon”. But, we live in a world inundated with truths that are suppressed because they are too emotionally charged or don’t fit the standards of civil society, so it isn’t much of a stretch to understand why the archetype of comedy has a tendency to manifest with the involvement of Pluto.
With Bill, Pluto is opposing his Venus, the ruler of his chart and conjunct Jupiter, the planet representing the archetype of faith and religion. Also, both Jupiter and Pluto are retrograde, highlighting how Bill has merged and internalized their archetypal concepts and used the tension of their awareness (opposition) in how he projects himself (Venus, Asc ruler) into what he creates (5th house) in order to propel his career (Venus-Moon-MC aspects).
All three of these planets are in square aspect to Bill’s Mars-Saturn Sagittarius conjunction in the 3rd house of communication and localized information or observation. Sagittarius is a sign focused on higher truth and with Mars placed in this sign, this focus is being expressed through the archetype of aggression or courage and conjunct Saturn, the ruler of his 5th house of creativity, echoing and connecting the theme represented by his 5th house Venus.
With this conjunction positioned in the 3rd house, Bill doesn’t believe in what he can’t see (the strictness of Saturn) and these apex dynamics are the main drivers for the atheism (along with Neptune’s involvement from the grand square) that deeply influences his creativity and career.
Does all of this cause friction with others? Without a doubt. The square aspect between Mars and Venus is a focus of attention as it is the tightest aspect in the chart, it is a classic significator for relationship issues and specifically rules Bill’s 1st and 7th house of self and others. Most notably, Bill’s aggressive and blunt style of communication resulted in the cancellation of his earlier show, Politically Incorrect, due to comments shortly after 9/11 that many thought were inappropriate.
 At its most basic, Libertarianism promotes a vision of simplified government and has been one of Bill’s historic favorite political philosophies.
 Also, Aquarians tend to enjoy a group structure and the panel format of Bill’s Real Time show allows him the environment in which to shine his ego the strongest.
 Historically, astrology suffers from an inability to exactly quantify the quality of its characteristics. When we say something is “really” this way or that and then something similar is not, critics quickly qualify the other as a “miss” because there is not a clear method to assign a numerical value to the subtle differences of magnitude that may taint the comparison. Bill’s grand square stands out in field of “regular” grand squares because it involves two of the most powerful personal archetypes in his chart in addition to being angular.
 Bill’s scepticism of spirituality, support of atheism and admitted use of marijuana are also represented by this relationship.
 When individuals are this closely enmeshed with the outer planets, they have the potential to embody the archetypes as their relationship to them matures.
 Absurdism, which provides a philosophical foundation for comedy, was conceived by Albert Camus, a Scorpio Sun. Its ruler, Pluto, was conjunct his midheaven.
 As the old adage goes, “there’s a lot of truth in jokes”.
 Venus is a strong intersection point between the grand square and t-square.
 It should also be noted that one of his favorite topics to attack (Mars) is political correctness because of its censorship (Saturn, restriction) of our communication (3rd house).
 When you consider Saturn’s involvement, it is understandable why Bill has never been married. His interpersonal relationships have the potential to turn into battle fields.