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Little 500: Entertainers of the Past

There’s a little event going on in town this week.

 Black and white photograph of students celebrating after the Little 500 race.

Yep, it’s time for Little 500 at Indiana University, for many years called the World’s Greatest College Weekend.

The race was the brainchild of Howard “Howdy” Wilcox. Wilcox, Director of the IU Foundation (IUF), established the IU Student Foundation Committee in 1950 in order to raise awareness of the Foundation and its purpose. He saw the race as an opportunity to publicize the IU Student Foundation and raise scholarship money for students working their way through school. The bike race, modeled after the Indianapolis 500, was first run in 1951. The first years featured only the race but before long a Variety Show was added and in subsequent years additional entertainment and events were developed, including the Golf Jamboree (1958), the Cream and Crimson intra-squad football game (1963), and the Style Show (1969).

This year there has been a tremendous amount of excitement over the headliner Lil Wayne and I thought there might be some interest in learning a bit about the past acts that have come for Little 500. In 1953, IUF Director Bill Armstrong decided to add a little celebrity luster and brought in the first Little 500 Sweetheart, actress and singer Lu Ann Simms. Simms was given every photo op possible throughout the weekend.

Actress and singer Lu Ann Simms served as the first Little 500 Sweetheart in 1953.

With the crowds the race began to draw, Armstrong harbored concerns about what folks could do in town post-race, so two years later he added a Variety Show. The headliner that year was Horace Heidt and his 50-person “Swift Show Wagon.” The group performed at the Auditorium and a new tradition was born. Feeling there could still be more, in 1960 Armstrong launched the Friday night concert, the Little 500 Extravaganza. The first performers were The Four Lads, who entertained crowds from the Woodlawn tennis courts.

In his book, The Little 500: The Story of the World’s Greatest College Weekend, author John Schwarb relays the story of Armstrong’s greatest celebrity coup, Bob Hope. Schwarb writes, “Making a personal crusade out of landing the big act of the day, he traveled to Hope’s North Hollywood, California, home in early 1963 to personally ask for the star’s attendance. Initially Hope rebuffed Armstrong’s request, saying that IU couldn’t be anywhere near as great as advertised, and that the school up the road in West Lafayette was better.” [this archivist’s response: *gasp*] Armstrong continued to pursue Hope and he agreed to come in 1964. That year, Little 500 set an attendance record of 23,790 and Hope delivered with four shows to accommodate the deluge of ticket sales. But when Armstrong in turn delivered his $30,000 check, Hope tore it up. Turned out he had such a great time that he asked to return the next year and did so again in 1967, 1971, and 1975, donating his fees to a scholarship fund in his name. (Interested in applying? Check out

The McGuire Sisters were 1954's Little 500 Sweethearts.

So, there have been a lot of celebrities connected to Little 500. Some other names of the past:

  • 1955: Horace Heidt’s Swift Show Wagon
  • 1958: headliners Don Cherry & Tina Robin; Popoff Teddy Family, and Al Cobine
  • 1965: The Kingsmen
  • 1969: Tony Bennett, George Kirby, and the Sandpipers
  • 1970: Chicago
  • 1978: Lou Rawls
  • 1983: Barbara Mandrell & the Do-Rites
  • 1988: Innuendo, the Cones, & Voyage
  • 1992: Larry Crane, Henry Lee Summer, and John Mellencamp
  • 1993: The BoDeans (openers were Material Issue & The Why Store)
  • 2001: Nelly
  • 2005: The Roots
IU alums, what were some of your favorite Little 500 shows?


  • Craig says:

    Mellencamp 1986 in memorial stadium.

  • Dina Kellams says:

    Hi Ron! I pulled the scrapbook for the 1967 Little 5 and it says entertainers that year were Bob Hope, Vic Damone, Nancy Ames, and the Association. On Friday evening, The Buckinghams played at the “Extravaganza” at the Fieldhouse parking lot. I’ll also follow up with an email!

  • Ron Hampton says:

    I was at the 1967 concert with Bob Hope; he was fabulous. But I cannot recall if the bad was The First Edition or The New Christie Minstrels. If any others were there and remember, drop me a line at Class of 1969!

  • Sue says:

    These groups were usually Saturday night after the race. I was wondering what the music (party ) was called in the field house that was pretty rowdy as I remember. Here’s towards students and usually a well know rock group……this was Friday night ….

  • Tom Boscher says:

    I remember The Kingsmen performing on the loading dock behind one of the cafeterias in 1965. Open air. No cost. Great time to be in Bloomington.

  • Dina Kellams says:

    Hi Nina!
    I checked the program and in 1987, IUSF and Union Board Concerts organized the “Little Five Live” and Food Fair. It was “a three house showcase of three of the area’s hottest bands.” Performers were Kilo, Dr. Bop and the Headliners, and Voyage. Additionally, MTV was there “for the second year in a row.”

    Fun question, thanks!!

  • Nina feigen says:

    Trying to find the name of a band that performed at little 500 in 1987

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