That's likely the way you've heard of Charlie Grimm, who in one form or another (player, manager, broadcaster, banjo-strummer, all-around ambassador) was associated with the Chicago Cubs for nearly fifty years.
But before he obtained that "jolly" image, Grimm was a solid first baseman for two decades (offensively, much in the mold of a Mark Grace-type of hitter), and a good manager who led the Cubs to three pennants. Only Frank Chance (four) and Cap Anson (five) had more, and in fact, between Chance, Grimm and Anson, that accounts for the managers of twelve of the sixteen Cub NL pennants (Fred Mitchell, Joe McCarthy, Gabby Hartnett and Al Spalding managed the four others). And Grimm also knew when to leave -- in 1938, with the club struggling in third place on July 20 with a 45-36 record, he stepped down, and Hartnett led the Cubs to the 1938 pennant.
Charles John Grimm was born on August 29, 1898 in St. Louis. As did many boys in those days, he became a bat boy there, and was eventually signed to play for the Philadelphia A's by Connie Mack. At the age of 17 he had 22 at-bats for the 1916 A's (one of the worst teams in baseball history -- they went 36-117 and finished 54.5 games out of first place), then returned home, played a few games for his hometown Cardinals in 1918, before signing with the Pirates, where he became their regular first baseman in 1921.
Three years later, he was, in one of the best deals the Cubs made in that era, dealt to Chicago after the 1924 season along with Wilbur Cooper and Rabbit Maranville in one of those "good for both teams" deals. The Pirates got Vic Aldridge, George Grantham, and Al Niehaus; Aldridge and Grantham were key parts of the 1925 and 1927 Pirate NL champions.
Grimm, meanwhile, entrenched himself at first base for the Cubs, and by 1932, at the age of 33, he replaced the largely-disliked Rogers Hornsby as manager, leading the club to the 1932 pennant after Hornsby had them muddling around second place with a 53-46 record. Grimm led the Cubs to a 37-18 mark and the flag; he also hit .307/.349/.425 that season, one of his best seasons as a player.
With the demands of managing and the fortuitous signing of 18-year-old Lane Tech phenom Phil Cavarretta, Grimm's playing time dwindled after 1933, and he retired as a player after the 1936 season with 2299 hits and a lifetime .290 average. He continued managing until, as mentioned above, the team struggled through the first half of 1938, then he voluntarily stepped aside for Gabby Hartnett -- imagine that happening today; you can't. This was the product of an era gone by, when a gentleman might realize he wasn't the best man for the situation, and put the team's interest above his own. It helped give the Cubs another pennant.
After that, Grimm got into broadcasting, and also went into partnership with Bill Veeck; the two bought the then-minor league Milwaukee Brewers in 1941. Grimm also managed the team.
Returning to the Cubs in 1944, Grimm managed the last Cub pennant-winning team in 1945. By then his reputation as a clown was beginning to form; Cubs management "looked the other way" at this, as it was a way of putting people in the seats as the team's fortunes began to decline after 1945. According to Grimm's New York Times obituary:
"Then Marvin Rickert tripled to right," the columnist wrote. "He could have made the bag standing up. But Grimm, coaching at third, signalled frantically to Rickert that he should hit the dirt. The base runner let go with a beautiful slide. At the same instant, Grimm leaped from the coaching box and slid into the bag, too. The crowd roared in delight."
You just don't see that sort of thing at the ballpark any more, nor am I arguing you should. But Grimm -- being the polar opposite of the meaning of his name -- knew that baseball was entertainment, and in that era, a more casual one than today's, such things were more accepted. Perhaps they also helped in some way to give the Cubs the image as "lovable losers". By 1949, lovable or not, they were losers, and Grimm was dismissed as manager. Three years later, he wound up in Boston as manager of the then-sad sack Braves; he came with them when they moved to Milwaukee in 1953, and had three solid seasons as manager in 1953, 1954 and 1955. But again, after a slow start in 1956, he was fired, replaced by Fred Haney, who would get the glory as the first manager to lead the Milwaukee Braves to the World Series.
And so, Grimm was drawn back to the Cubs one more time -- at age 61, he was named manager for the 1960 season. Glory years long since gone, he managed the club for the first seventeen games of the season, going 6-11, and then was involved in one of the most unusual swaps in baseball history. He and Lou Boudreau, then in the WGN radio broadcast booth, traded jobs.
This wasn't as silly as it seemed -- Grimm had had broadcast experience, and Boudreau had fifteen years' managing experience, taken a team to the World Series, and was only 42 years old. But that Cub team was atrocious, and Boudreau went back to broadcasting in 1961, while Grimm became one of the College of Coaches, although he never served as "head coach".
Grimm's Wikipedia entry contains the allegation that, as part of the College of Coaches and with influence with management, helped to prevent Buck O'Neil, who was a coach in 1962, from becoming head coach under the rotating system. I have not been able to find any corroborating evidence for this; if true, it would have prevented O'Neil from becoming (essentially, in fact if not in name) the first black manager in baseball history.
Grimm continued to be associated with the Cubs as a consultant to various general managers, up to and including Dallas Green, who was GM when Grimm died on November 15, 1983 in Scottsdale, Arizona. After fifty years' association with the Cub franchise, Grimm is now literally part of Wrigley Field. His widow asked for and received permission to spread his ashes at the ballpark.
There is much talk today about eventually inducting Joe Torre into the Hall of Fame for his combined body of work as a player and manager. Charlie Grimm's twenty-year playing career and nineteen-year managing career hold up well in comparison to Torre's -- the only thing he failed to do that Torre has accomplished, though he got there three times, was to win a World Series.