Trivia: Known for his confrontational style, political commentator Bill O'Reilly's career in journalism begun in the 1970s, when he worked as a reporter and columnist for several newspapers and local publications during his college years at Boston University. A far cry from his later position as a key figure in mainstream conservative media, some of O'Reilly's early years in broadcasting were spent as a movie critic and entertainment writer for The Miami Herald. After working as a news correspondent for television stations in Pennsylvania and Texas, CBS sent O'Reilly to Argentina to cover the wars in El Salvador and the Falkland Islands. O'Reilly's career continued to grow throughout the 1980s, but his "big break," so to speak, came in the form of Inside Edition, a tabloid gossip and news program in the same vein as A Current Affair. After replacing David Frost as Inside Edition's anchorman, O'Reilly went on to cover various historic milestones, including the Los Angeles riots and the fall of the Berlin Wall. O'Reilly chose to further his education in the mid-'90s, ultimately earning a master's degree from the prestigious Harvard University. Shortly afterward, O'Reilly met a pivotal figure in his career: Roger Ailes, chairman and CEO of the Fox News Channel. Ailes hired O'Reilly to anchor The O'Reilly Factor, which quickly became the standard in a growing arena of political media, particularly among conservatives. The Factor's popularity spawned numerous book deals and contributed heavily to the popularity of O'Reilly's similarly formatted radio show. Perhaps the surest mark of success, Bill O'Reilly's trademark aggression toward his interviewees and a multitude of government figures eventually served as inspiration for Stephen Colbert, who modeled his television persona on the highly popular Colbert Report after O'Reilly. Colbert affectionately referred to O'Reilly as "Papa Bear."In 2010, O'Reilly was ranked number four on Newsweek's "Power 50" list of the 50 highest-earning political figures of the year.

Trivia: Bill Maher is best known for hosting the irreverent, often wickedly funny late-night talk show, Politically Incorrect, in which Maher leads a wide variety of celebrities in a discussion of politics and modern issues. The New Jersey-native began as a standup comic (it still remains his first love) and in 1979 worked as a host at the Catch-a-Rising-Star comedy club in New York. In 1982, he was discovered by comedian Steve Allen and this led to Maher's appearances on Johnny Carson's Tonight Show and on David Letterman's late-night talk show. Maher also tried his hand at acting, appearing as a guest star on television series in the late '80s, including Newhart, Roseanne, and Married With Children. He made his feature-film debut in D.C. Cab (1983) and went on to appear in such films as Cannibal Women in the Avocado Jungle of Death (1988) and Pizza Man (1991). He began hosting and writing for Politically Incorrect in 1994. The show would run until 2002, and Maher would pick up where he left off the next year, with Real Time with Bill Maher.

Trivia: Covered the OJ Simpson case, the International War Crimes Tribunal from the Netherlands, and the assisted-suicide trials of Dr. Jack Kevorkian from Michigan while working as a resporter for Court TV from 1994 to 1997.Founded Abrams Media Network in 2009.Is the Chief Legal Affairs Anchor for ABC News.Published his book Theodore Roosevelt for the Defense: The Courtroom Battle to Save His Legacy in May 2019 and it became an immediate New York Times bestseller.Has published articles in The Wall Street Journal, The New York Times, The American Lawyer, USA Today magazine, and the Yale Law and Policy Review.

Trivia: Started out as a producer for hip-hop artists including Jermaine Dupri, Jay-Z and Ludacris. After fracturing his jaw in a car crash, he wrote "Through the Wire," which got him a record deal. Walked out of the American Music Awards in 2004 after losing the Best New Artist award to country performer Gretchen Wilson. He later apologized to her for his actions. Took some heat for publicly criticizing President George W. Bush during a 2005 NBC Hurricane Katrina benefit concert. Was widely denounced when he interrupted Taylor Swift's acceptance speech at the MTV Video Music Awards in September 2009. Made his directorial debut in 2010 with the musical short film Runaway, which is based on the song of the same name from his My Beautiful Dark Twisted Fantasy album.

Trivia: As an actor, writer, producer, and director of films and stage plays, the New Orleans-born Tyler Perry began his career as a dramatist in 1992. When inspired by Oprah Winfrey to channel his creativity through writing, Perry put pen to paper as a method of healing the wounds that lingered from a painful childhood. His first production, entitled I Know I've Been Changed, hit the stage to rapturous reviews in 1997, and following a collaborative period with Bishop T.D. Jakes that resulted in the plays Woman, Thou Art Loosed and Behind Closed Doors, Perry flew solo to create cantankerous 68-year-old grandmother Mabel "Madea" Simmons (whom Perry played, in full drag) in I Can Do Bad All by Myself around 2000 A slew of Madea-based projects were quick to follow, and shortly thereafter Perry joined Grammy Award-winner Kelly Price for the play Why Did I Get Married?. His plays garnered countless fans thanks to Perry's trademark practice of releasing them on home video. Throughout this period, many credited Perry with resuscitating (and reinventing) African-American theater; in the process, Perry's first eight plays reportedly earned a cumulative gross of over 75 million dollars in ticket and video sales.Perry didn't fully enter the public spotlight, however, until he cropped up in mid-2005 with the oddball A-lister Diary of a Mad Black Woman, self-adapted from his own hit play. This story of an African-American woman Helen McCarter (Kimberly Elise) struggling to rebound after a painful separation, whose life is invaded (in more ways than one) by the obnoxious, loudmouthed, chainsaw-wielding (!) Madea, Diary -- a bizarre combination of domestic melodrama, violent, racially-oriented farce, and Christian proselytizing -- understandably left many critics running for the exit, but, of course, ticket buyers prevailed. The film scored with its intended African-American audience and grossed a healthy 50 million dollars (it ranked as number one at the box office during February 2005), leading to an early 2006 sequel, Madea's Family Reunion, this one written and directed by Perry. Either because Perry's talent had matured within a year or because the press had grown accustomed to the playwright-cum-filmmaker's defiantly unconventional style, critics were slightly kinder about the sophomore Madea outing, which benefits from finely-felt supporting turns by the legendary Cicely Tyson and Maya Angelou. Like its predecessor, Reunion struck box office gold, and even topped Diary's net, reeling in an estimated 63.3 million dollars in international grosses. Perry then scrapped the Madea character for a tertiary cinematic outing, Tyler Perry's Daddy's Little Girls. This romantic dramedy concerns Monty (Idris Elba), a financially strapped African-American mechanic who loses custody of his children to his drug-pushing ex-wife, and then falls in love with the beautiful attorney (Gabrielle Union) whom he hires to get the children back. Increasingly prolific on stage and screen in the following years, Perry continued packing fans into theaters with Madea Goes to Jail (2009), I Can Do Bad All By Myself (also 2009), Good Deeds (2012) and Madea's Witness Protection while simultaneously making a mark on television as creator of the hit sitcom Tyler Perry's House of Payne. Perry also began to take some acting roles in films that he didn't write/direct/producer, like the titular character in Alex Cross (2012) and a supporting role in David Fincher's Gone Girl (2014).

Trivia: As an advocate of black comedians' talent, D.L. Hughley worked to support their careers, leading by example. After years of experience in the standup circuit, Hughley took on the role of host of BET's Comic View in 1992, in addition to various other television appearances on comedy programs and sitcoms. He was born on March 6, 1963, named Darryl Hughley, and raised in Southern California, where he would spend the majority of his performing life as well. On February 22, 1986, he wed his wife LaDonna, with whom he had three children.Once Hughley had gained some attention as a standup comedian, he appeared on an HBO special, which led to his status as host of Comic View. In 1995, he played Marlon on the TV series Double Rush, and starred in his self-monikered sitcom The Hughleys as himself in 1998. The following year, he performed the voice for the Gadgetmobile in the live-action film Inspector Gadget (starring Matthew Broderick), inspired by the 1980s cartoon series of the same name.He appeared in the Spike Lee documentary The Original Kings of Comedy, which also featured several other accomplished black comedians including Steve Harvey, Cedric the Entertainer, and Bernie Mac. In 2001, Hughley expanded his performance horizons with his role in the dramatic comedy The Brothers, a film by Gary Hardwick exploring the realms of friendship and marriage. After The Hughleys wrapped in 2002, he continued to remain a constant fixture in the comedy scene, appearing in additional films like 2004's Soul Plane. He also took on the recurring role of Simon Stiles on the critically acclaimed but short-lived Studio 60 on the Sunset Strip in 2006 and 2007 as well as the comedy series Glory Daze in 2011. Venturing back into film, Hughley signed on to appear in the action comedy Cat Run later that same year.

Trivia: Started his career as a print journalist for the Winston-Salem Journal. Became a Philadelphia 76ers columnist for The Philadelphia Inquirer in 1994. Launched his television career as a host on CNN/SI in 1999. Played the role of a television reporter on General Hospital in its February 2, 2007 episode. Became the permanent host of ESPN's First Take on April 30, 2012. Signed a multi-year deal with ESPN in 2014 which pays him $3 million annually.

Trivia: Grew up in Carville, LA, a town on the Mississippi River named for his grandfather, who was its postmaster. As a teen, he worked on his first political campaign for a car dealer running for the Louisiana state legislature. Served in the United States Marine Corps from 1966 to 1968. Taught eighth-grade science in rural Louisiana. Has appeared as himself on Mad About You, Spin City, The Family Guy and Arli$$. Played a prosecutor in Milos Forman's 1996 film The People vs. Larry Flynt. Had a cameo in the 2005 comedy Wedding Crashers. Both he and his wife, GOP stalwart Mary Matalin, hosted CNN's raucous Crossfire, but not at the same time. A prolific author, his books include such New York Times best sellers as We're Right, They're Wrong (1996), and a children's book, Lu and the Swamp Ghost (2004). In 2009, joined the faculty of Tulane University to teach political science.