- According to himself, when his show Love Connection (1983) was canceled, of the roughly 22,000 couples who met on the show, there were a total of 29 marriages, 8 engagements, and 15 children.
- While in the hospital, he tried to commit suicide.
- Missed a week's worth of episodes of Wheel of Fortune (1975), because he was in the hospital, hence, Alex Trebek subbed for him.
- Worked 39 days per year while hosting Love Connection (1983).
- Over 2,000 episodes of Love Connection (1983) were taped in the 11 years he hosted the show (1983-1994), making it one of the longest lasting game shows in syndication.
- Father, with Margaret Hayes, of Cary, Katherine and Chad, who died in a motorcycle accident in 1986 at age 19; father, with Jo Ann Pflug, of daughter Melissa; father, with Teri Nelson Carpenter, of sons Michael and Sean.
- On September 23, 1996, Woolery underwent quadruple-bypass heart surgery in Los Angeles.
- Wrote 1968 hit (Billboard #40) "Naturally Stoned" by studio group Avant-Garde.
- At one point, he was going to be a guitarist and singer.
- Ranked #8 as GSN's Top 10 Game Show Hosts of All Time.
- He, alongside Bob Eubanks and Jamie Farr, was one of the three rotating hosts of the $250,000 Game Show Spectacular at the Las Vegas Hilton, until the show closed in April 2008.
- Made a successful comeback with Love Connection (1983), after a two-year absence on television.
- Best known by the public as the host of Wheel of Fortune (1975), Love Connection (1983), Scrabble (1984) and Lingo (2002).
- Before he was a game show host, he was a singer and an actor.
- Had a quadruple heart bypass operation on September 23, 1996.
- In the mid-1960s, he moved to Nashville, Tennessee, to become a musician.
- As of 2016, he is the first game show emcee to have hosted four long-running shows.
- Received a letter from Bob Barker who wanted to express his condolences about one of Woolery's three sons, Chad, who died in an motorcycle accident in 1986.
- Spokesman, "Generation America".
- Had appeared on Match Game/Hollywood Squares Hour (1983), just a few days before he began hosting Scrabble (1984) for NBC.
- With Jo Ann Pflug, he appeared alongside Bill Cullen and his wife Ann Mocamber along with Allen Ludden and his wife Betty White on Tattletales (1974) in 1974.
- In addition to writing the #40 hit "Naturally Stoned" by the duo "The Avant-Garde", he was one half of the duo, along with Elkin Thomas Fowler (better known as Elkin 'Bubba' Fowler).
- His idols when he was very young were Bill Cullen and his ex-brother-in-law Tom Kennedy.
- Is one of the founders of the political action committee Restart Congress, along with, among others, Michigan's 41st Secretary of State, Terri Lynn Land.
- Former son-in-law of David Nelson.
- His longest lasting game show is Love Connection (1983). He hosted that show for 11 years (1983-1994). He hosted Scrabble (1984) on NBC for 7 years (1984-1990, 1993) and was the first host of Wheel of Fortune (1975) (1975-1981) before he left after a contract dispute with creator Merv Griffin (Pat Sajak took over and still is the host today). Woolery's most recent game show outputs were a short lived syndicated revival of The Dating Game (1997) from 1998 to 2000 and the big money game show Greed: The Series (1999) on FOX from 1999 to 2000. Starting in August of 2002, Chuck has been hosting Lingo (2002) on Game Show Network (GSN).
- A new version of Love Connection (1983) was attempted from 1998-1999. Comedian Pat Bullard took over the hosting from Woolery. Though it retained the original format, viewers unfamiliarity with Bullard and late night time slots in most markets hindered the show, and it ceased production after only one season.
- Friends with: Michele Lee, Vicki Lawrence, Betty White, Bob Barker, Bob Eubanks, Bob Goen, Bill Cullen, Richard Dawson, Jim Lange, Jim Perry, Tom Kennedy, Geoff Edwards, Wink Martindale, Bill Rafferty, Peter Tomarken, Merv Griffin, Mark Goodson, Alex Trebek, Pat Sajak, Pat Finn, Monty Hall, Regis Philbin and Dick Clark.
- Graduated from Ashland High School (now Paul G. Blazer High School) in Ashland, Kentucky, in 1959.
- Before he was a successful game show host, he worked as a wine consultant for Wasserstrom Wine & Import Company in Columbus, Ohio.
- In Hollywood taping a new season of Lingo (2002) on the Game Show Network (GSN) cable network. (August 2005)
- Went to high school with future basketball player Harold Sergent.
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