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An updated ranking of the worst 7th-inning stretch singers in Wrigley Field history

There have been many cringeworthy versions of “Take Me Out to the Ball Game” at Wrigley Field, but these are the baddest of the bad.

Former Bears coach Mike Ditka gave a memorably speedy version of “Take Me Out to the Ball Game.”
Sun-Times

It helps to know the song.

Leading the crowd in the singing of “Take Me Out to the Ball Game” during the seventh-inning stretch, a tradition popularized by the legendary Harry Caray, has become a Wrigley Field institution.

Caray first sang on the South Side when he broadcast games for the White Sox. Then he brought the ritual with him to the Cubs and immortalized it at the Friendly Confines.

In the years since his death in 1998, the Cubs have continued the tradition of having “Guest Conductors” lead the stretch singing. It started as a tribute to Caray, but has morphed into an opportunity for any celebrity in town to promote an upcoming project or shill for some random product.

There have been many infamous renditions of the song by celebrities over the years where things have taken a turn for the worst. But we wanted to look back at the worst of the worst.

You don’t have to be a great singer — Harry definitely wasn’t — but some passing familiarity with the tune and/or lyrics is useful.

In general, to live in seventh-inning infamy, a celebrity must be memorable and screw up in some way. Mixed martial arts fighter Conor McGregor is the latest celebrity to serve up a less-than-stellar rendition.

Some tips for celebrities: Don’t be late (Ditka), don’t rush through the song (Mr. T), make sure you “root, root, root for the Cubbies” and not some other team, remember the correct name of the venue (Hi, Jeff Gordon!) and be somewhat coherent.

But when all else fails, enthusiasm masks ineptitude.

Here is our countdown of the worst all-time seventh-inning stretch guest conductors:

6. Sept. 21, 2021: Conor McGregor

The MMA fighter is originally from Ireland so he gets some slack because this was seemingly his first-ever baseball game. Not the best singer, he truly made the song his own — his own tune, lyrics and tempo — in this idiosyncratic rendition. However, the master showman had fun and his charm, charisma and enthusiasm won the day.

5. May 25, 2009: Mr. T

A less-than-tuneful version, Mr. T sped through the song and did give us the memorable line “One, two, three strikes YOU OUT!”

4. Aug. 7, 2001: Steve “Mongo” McMichael

The Bears great holds the notorious distinction of getting ejected by home-plate umpire Angel Hernandez after a call went against the Cubs. “I’ll have some speaks with that home-plate umpire after the game,” he said. His singing was fine, but his threatening the umpire will be long remembered.

3. May 24, 2005: Jeff Gordon

He started off with a cringe-worthy moment by calling it “Wrigley Stadium.” But the actual singing was worse. The NASCAR legend stopped singing in the middle of the song, but the music played on. He got hopelessly behind, lost the increasingly hostile crowd, never recovered and was booed out of the booth. Always remember “Wrigley Stadium.”

2. July 5, 1998: Mike Ditka

During the first year of guest conductors, the iconic former Bears coach was late, leaving Steve Stone and Chip Caray to momentarily filibuster, before Da Coach made his fashionably late arrival. When he did take the mic, he made up his missed time with a speedy 22-second version. Wrigley Field organist Gary Pressy called it his “most memorable accompaniment.”

1. Aug. 17, 2003: Ozzy Osbourne

The Black Sabbath singer turned reality star is the undisputed worst ever. His charmingly bad version had players in both dugouts rubbernecking to see the train wreck. You knew it was going to be memorable when he started “let’s go out to the ballgame.” He then mumbled and hummed his way through the majority of the song before somewhat finding his way at the end.

Still none can compare to the original — the great Harry Caray: