The combination of his horrendous singing and the fact that he's not very popular in Chicago after his 329-yard game against the Bears last year got him booed as loudly as any visiting player at Wrigley Field.
Romo grew up in Burlington, Wisconsin, 75 miles from Chicago, and he played at Eastern Illinois, and he's apparently a Cubs fan. But really, it's probably not the best idea to bring in football players for teams other than the Bears. Was there any doubt that they'd boo him?
Also: His singing voice is terrible. Jessica Simpson might want to work with him on that.
Tony Romo and Jessica Simpson
See photos of Tony Romo and Jessica Simpson
Tony and Jessica
Dallas Cowboys quarterback Tony Romo throws out the first pitch before a Chicago Cubs game against the Arizona Diamondbacks on May 11. Romo also sang "Take Me Out to the Ballgame."
Nam Y. Huh, AP
Romo and girlfriend Jessica Simpson celebrate Romo's 28th birthday with a kiss at a Dallas nightclub in April.
Robert Hart, ZUMA Press
The NFL quarterback and singer, seen here enjoying Romo's birthday cake, first started dating in November.
Robert Hart/ZUMA Press
Romo and Simpson cheer a three-point shot by the Dallas Mavericks in a game against the Los Angeles Lakers in March.
Ron Jenkins, Fort Worth Star-Telegram/MCT
Simpson and Romo clown around at a wedding party for Dallas teammate Bobby Carpenter in March.
X17online.com
Photographers catch a shy Romo and smiling Simpson in New York City in March.
James Devaney, WireImage.com
Simpson and Romo make their way through Los Angeles International Airport in March.
X17online.com
Jessica Simpson with Tony Romo arrive at a Hollywood restaurant a few weeks after Romo's Cowboys were bounced from the NFL Playoffs in January.
X17online.com
Simpson was widely criticized when the Cowboys season fell apart. Many felt the entertainer distracted the quarterback from his duties.
Edward A. Ornelas, San Antonio Express-News/ZUMA Press

Reader Comments ( Page 1 of 5)
1. Oh yea!!!! Jessica will help him to get better...Sorta like asking Walter Mondale to teach you how to win an election
Posted at 11:10PM on May 11th 2008 by carl
2. Jessica will not be able to help him. He sounds like he is a lost cause. Very funny though.
I didn't hear booing.
Posted at 11:34PM on May 11th 2008 by Diandra
3. Tony Romo makes Aaron Neville sounds like Englebert Humperdick by comparison.
Posted at 12:04AM on May 12th 2008 by George B Vieto
4. Well, now there's two things he can't do, sing and win a damn playoff game.
Posted at 12:07AM on May 12th 2008 by Xavier
5. it was so pathetic... it made me not want to watch the cubs game anymore... glad i did tho, hell of a comeback reed johnson is soooo good. Glad we dont have to watch jacque jones in outfield anymoe...
Posted at 4:49AM on May 12th 2008 by Brandon
6. At least he didn't call it Wrigley Stadium like Jeff gordon did.
Romo is an example of a guy who has a lot of talent but hasn't figured out yet how to manage his image. Joe Theisman had a similar problem early in his career but figured out how to overcome it.
Posted at 6:05AM on May 12th 2008 by al coholic
7. Please,Tony! Don't ever, ever, do that again ! I love you as My Cowboys Quarterback, but not as a singer! I'm sorry Cub Fans!
Posted at 10:04AM on May 12th 2008 by REBECCA COUCHMAN
8. If Tony Romo needs help with singing,he needs to get it from Carrie Underwood,NOT Jessica"I have no talent" Simpson.That's like getting Ray Charles and Stevie Wonder to drive each other cross country.Jessica Simpson is SOOOOOOOOO over rated,she's not pretty and has no clue that her boyfriend is still in love with Carrie.Tony,if you read this,DUMP JESSICA and go back to Carrie!!!!
Posted at 10:14AM on May 12th 2008 by Bambi
9. He isn't a Bear-so if there were boo's(and I didn't hear them either)it is simply that he is a Cowboy, not a Bear. I am just glad he did not drag that talentless bimbo with him. DoubleD's are great I guess-but you have to talk to her sometime and she is an idiot who makes Tom Cruise look like a nuclear physicist.
Posted at 10:14AM on May 12th 2008 by kathy warren
10. Just because the media hypes him as a great QB doesn't mean you should let him throw out the first pitch and just because the media hype up the fact that he's dating Jessica Simpson doesn't mean he can sing.
Posted at 10:16AM on May 12th 2008 by J.T.
11. Tony Romo? Who is he???
Posted at 10:25AM on May 12th 2008 by NumbrCrunchr
12. He didn't sing very well but how many celebrities (not professional singers) do sing good at the ball park? I also did not hear him get booed. Give him a break, he is a football player not a singer and if he is a Cub fan and a celebrity why not have him throw the first pitch?
Posted at 10:27AM on May 12th 2008 by Marly
13. SO baby boy Tony is tone deaf... he's not a singer.. he's a football player out having a good time... as long as he keeps doing what he does best... QB for the Cowboys.. he can sing in any tone or pitch he wants... We'll still love him!
Posted at 10:33AM on May 12th 2008 by Moondanser
14. Tony's a good down-to-earth guy and manages to stay out of trouble (unike other NFL players). What ever happened to just having fun and enjoying the game?
Posted at 10:38AM on May 12th 2008 by potomacsports
15. I heard booing a first but I didn't hear any booing when he sang. He is a football player, not a singer.
Posted at 10:40AM on May 12th 2008 by Jennifer
16. THAT WAS NOT BOOING IT WAS COYOTES HOLLOWING. IM A COWBOYS FAN AND IM GLAD HE DOES NOT SING IN DALLAS!!
Posted at 10:43AM on May 12th 2008 by eddieb
17. What is it that cubs fans do not understand about the song? The object is to sing it and not to be Bing Crosby. The game is the thing, and not the song.
I am not a Romo fan and it is good to see that there are lousy singers beside myself.
At least we wont have him making a mockery of the Star Spangled Banner like most of these so called singers.
Posted at 10:45AM on May 12th 2008 by George
18. TONY ROMO DOES NOT NEED A DEFENSE. EXCEPT ON THE FOOTBALL FIELD...HE IS THE DALLAS COWBOYS QB..AND WILL BE ONE OF THE GREATEST. I CAN'T WAIT FOR SEPTEMBER! JESSICA IS HIS CHOICE. SO BE IT. BUT HIS TALENT IS REAL AND YET TO BE AT ITS PEAK!
Posted at 10:45AM on May 12th 2008 by Terri Kaleta
19. I was at the game yesterday and trust me they booed his mercilessly. It had nothing to do with is singing voice he was booed because he is a QB for the Cowboys not the Bears.
Posted at 10:52AM on May 12th 2008 by Kristen
20. Get the songs "Wrigley Field", "Summer of our Lives" and 8 more on ITUNES - just search "Kevin Henrickson" or "Waveland Ave" it's on the Waveland Ave CD
Posted at 10:59AM on May 12th 2008 by cubscd