Caray caught his break when he landed a job with the National League St. Louis Cardinals in 1945 and, according to several histories of the franchise, proved as adept at selling the sponsor's beer as at the play-by-play description.

Caray teamed with former major-league catcher Gabby Street to call Cardinals games through 1950, as well as those of the American League St. Louis Browns in 1945 and 1946.

His subsequent partners in the Cardinals' booth included Stretch Miller, Gus Mancuso, Milo Hamilton, Joe Garagiola, and Jack Buck.

Immediately preceding the Cardinals job, Caray announced hockey games for the St. Louis Flyers, teaming with former NHL defenseman Ralph "Bouncer" Taylor.

On one occasion, Taylor temporarily ended his retirement when he volunteered to play goalie for the Flyers in a regular season game with the team from Minnesota.

In November 1968, Caray was nearly killed after being struck by an automobile while crossing a street in St. Louis; he suffered two broken legs in the accident, but recuperated in time to return to the broadcast booth for the start of the 1969 season.

[8] On Opening Day, fans cheered when he dramatically threw aside the two canes he had been using to cross the field and continued to the broadcast booth under his own power.

At a news conference afterward, during which he drank conspicuously from a can of Schlitz (then a major competitor to Anheuser-Busch), Caray dismissed that claim, saying no one was better at selling beer than he had been.

[11] He spent one season broadcasting for the Oakland Athletics, in 1970, before, as he often told interviewers, he grew tired of owner Charles O. Finley's interference and accepted a job with the Chicago White Sox.

Caray joined the Chicago White Sox in 1971 and quickly became popular with the South Side faithful and enjoying a reputation for joviality and public carousing (sometimes doing home game broadcasts shirtless from the bleachers).

[citation needed] During his tenure with the White Sox, Caray was teamed with many color analysts who didn't work out well, including Bob Waller, Bill Mercer and ex-Major League catcher J. C. Martin, among others.

The tandem proved to work so well that Piersall was hired to be Caray's partner in the White Sox radio and TV booth beginning in 1977.

Caray succeeded longtime Cubs broadcaster Jack Brickhouse, a beloved announcer and Chicago media fixture.

The timing worked in Caray's favor, as the Cubs ended up winning the National League East division title in 1984 with WGN-TV's nationwide audience following along.

Millions came to love the microphone-swinging Caray, continuing his White Sox practice of leading the home crowd in singing "Take Me Out to the Ball Game" during the seventh inning stretch, mimicking his mannerisms, his gravelly voice, his habit of mispronouncing or slurring some players' names—which some of the players mimicked in turn—and even his trademark barrel-shaped wide-rimmed glasses.

This led to his absence from the broadcast booth through most of the first two months of the regular season, with WGN featuring a series of celebrity guest announcers on game telecasts while Caray recuperated.

[15] However, Harry Caray died in February 1998, before the baseball season began, leaving the expected grandfather-grandson partnership in the broadcast booth unrealized.

There would only be a few people who could hear Caray sing: his broadcast partners, WMAQ Radio producer Jay Scott, and the select fans whose seats were near the booth.

[16] Many of these performances began with Caray speaking directly to the baseball fans in attendance either about the state of the day's game, or the Chicago weather, while the park organ held the opening chord of the song.

[18] Major League Baseball rolled out a holographic rendition of Caray performing the song for the Cubs' 2022 Field of Dreams Game against the Cincinnati Reds in Dyersville, Iowa.

when his team hit a home run or turned a difficult play on field; he trained himself to use this expression to avoid any chance of accidentally using profanity on the air.

The Carays expanded to a fourth generation in 2022 when Chip's twin sons Chris and Stefan were named broadcasters for the minor league Amarillo Sod Poodles.

[26] Caray cited the rumors of the affair as the real reason the Cardinals declined to renew his contract after the disappointing 1969 season.

Caray was rushed to nearby Eisenhower Medical Center, where he never woke up from his coma and died on February 18, 1998, 11 days away from his 84th birthday.

Illinois Governor Jim Edgar, Mayor Richard Daley, and Chicago Bears coach Mike Ditka were also in attendance.

Chip would eventually sign to be the St. Louis Cardinals announcer in 2023, when at the end of the season Chris and Stefan were given assignments for the Arizona Fall League.

On the Nickelodeon series Back at the Barnyard, news reporter Hilly Burford bears a strong resemblance to Caray, both in appearance and speech.

The recurring character Reverend Fantastic from the animated television series Bordertown bears an uncanny likeness to Caray in both appearance and speaking style.

Caray can be briefly heard in the 1986 film Ferris Bueller's Day Off, as a Cubs game is shown on a TV in a pizza parlor.

[44] In 1988, Vess Beverage Inc. released and sold a Harry Caray signature soda, under the brand "Holy Cow", complete with his picture on every can.