IN: Artis Leon Ivey Jr. (born August 1, 1963), known professionally as Coolio, is an American rapper, actor, chef, and record producer. Coolio achieved mainstream success in the mid-to-late 1990s with his albums It Takes a Thief (1994), Gangsta's Paradise (1995), and My Soul (1997). He is best known for his 1995 Grammy Award-winning hit single "Gangsta's Paradise", as well as other singles "Fantastic Voyage" (1994), "1, 2, 3, 4 (Sumpin' New)" (1996) and "C U

In 1996, Coolio appeared on the Red Hot Organization's compilation CD America is Dying Slowly, alongside Biz Markie, Wu-Tang Clan, and Fat Joe, among many other prominent hip-hop artists. The CD, meant to raise awareness of the AIDS epidemic among African American men, was heralded as "a masterpiece" by The Source magazine. That same year, he recorded the theme song and appeared in the opening sequence of the Nickelodeon TV series Kenan & Kel which ran for four seasons.  After the success of Gangsta's Paradise, Coolio's next album was expected to be another hit. His third solo album titled My Soul, came out in 1997. Although it contained the major hit "C U When U Get There" and the album went platinum, it failed to reach the success of his previous two albums. Coolio was dropped from Tommy Boy Records and his albums since then, 2001's Coolio.com, 2003's El Cool Magnifico, 2006's The Return of the Gangsta, and 2008's Steal Hear, have not charted on any Billboard chart. He did have a minor hit in the UK in 2006 with "Gangsta Walk" (featuring Snoop Dogg), which peaked at #67 on the UK pop chart.  While touring with hip hop duo Insane Clown Posse, Coolio received a tattoo as a homage to the group's fanbase, reading "Jugalo Cool" [sic]. He stated that the misspelling was intentional. Coolio has performed at the Gathering of the Juggalos.  Coolio was featured on an international collaboration track called 'Fuck the DJ' by UK rapper Blacklisted MC also featuring Bizarre of D12, Adil Omar (from Pakistan) and Uzimon (from Bermuda) the song was premiered on music website Noisey from Vice in October 2014.
QUESTION: How was he associated to Tommy Boy?
IN: Hartman was born Philip Edward Hartmann (later dropping one "n") on September 24, 1948, in Brantford, Ontario, Canada. He was the fourth of eight children of Doris Marguerite (Wardell) and Rupert Loebig Hartmann, a salesman specializing in building materials. His parents were Catholic and raised their children in that faith. As a child Hartman found affection hard to earn and stated: "I suppose I didn't get what I wanted out of my family life, so I started seeking love and attention elsewhere."

Working alone as a graphic artist, Hartman frequently amused himself with "flights of voice fantasies". Citing the need for a more social outlet for his talents, Hartman, aged 27, began in 1975 to attend evening comedy classes run by the California-based improvisational comedy group The Groundlings. While watching one of the troupe's performances, Hartman impulsively decided to climb on stage and join the cast. After several years of training, paying his way by re-designing the group's logo and merchandise, Hartman formally joined the cast of The Groundlings; by 1979 he had become one of the show's stars.  Hartman met comedian Paul Reubens and the two became friends, often collaborating on writing and comedic material. Together they created the character Pee-wee Herman and developed The Pee-wee Herman Show, a stage performance which also aired on HBO in 1981. Hartman played Captain Carl on The Pee-wee Herman Show and returned in the role for the children's show Pee-wee's Playhouse. Reubens and Hartman made cameos in the 1980 film Cheech & Chong's Next Movie. Hartman co-wrote the script of the 1985 feature film Pee-wee's Big Adventure and had a cameo role as a reporter in the film. Although he had considered quitting acting at the age of 36 due to limited opportunities, the success of Pee-wee's Big Adventure brought new possibilities and changed his mind. After a creative falling-out with Reubens, Hartman left the Pee-Wee Herman project to pursue other roles.  In addition to his work with Reubens, Hartman recorded a number of voice-over roles. These included appearances on The Smurfs, Challenge of the GoBots, The 13 Ghosts of Scooby-Doo, and voicing characters Henry Mitchell and George Wilson on Dennis the Menace. Additionally Hartman developed a strong persona providing voice-overs for advertisements.
QUESTION: Did anything significant happen in his early career?
IN: The Algonquin Round Table was a group of New York City writers, critics, actors, and wits. Gathering initially as part of a practical joke, members of "The Vicious Circle", as they dubbed themselves, met for lunch each day at the Algonquin Hotel from 1919 until roughly 1929. At these luncheons they engaged in wisecracks, wordplay, and witticisms that, through the newspaper columns of Round Table members, were disseminated across the country. Daily association with each other, both at the luncheons and outside of them, inspired members of the Circle to collaborate creatively.

In addition to the daily luncheons, members of the Round Table worked and associated with each other almost constantly. The group was devoted to games, including cribbage and poker. The group had its own poker club, the Thanatopsis Literary and Inside Straight Club, which met at the hotel on Saturday nights. Regulars at the game included Kaufman, Adams, Broun, Ross and Woollcott, with non-Round Tablers Herbert Bayard Swope, silk merchant Paul Hyde Bonner, baking heir Raoul Fleischmann, actor Harpo Marx, and writer Ring Lardner sometimes sitting in. The group also played charades (which they called simply "The Game") and the "I can give you a sentence" game, which spawned Dorothy Parker's memorable sentence using the word horticulture: "You can lead a horticulture but you can't make her think."  Members often visited Neshobe Island, a private island co-owned by several "Algonks"--but governed by Woollcott as a "benevolent tyrant", as his biographer Samuel Hopkins Adams charitably put it--located on several acres in the middle of Lake Bomoseen in Vermont. There they would engage in their usual array of games including Wink murder, which they called simply "Murder", plus croquet.  A number of Round Tablers were inveterate practical jokers, constantly pulling pranks on one another. As time went on the jokes became ever more elaborate. Harold Ross and Jane Grant once spent weeks playing a particularly memorable joke on Woollcott involving a prized portrait of himself. They had several copies made, each slightly more askew than the last, and would periodically secretly swap them out and then later comment to Woollcott "What on earth is wrong with your portrait?" until Woollcott was beside himself. Eventually they returned the original portrait.
QUESTION:
What else did they do?