Build Your Baby Boomer Dream Team, and We’ll Guess How Old You Are

By: Teresa McGlothlin
Estimated Completion Time
5 min
Build Your Baby Boomer Dream Team, and We’ll Guess How Old You Are
Image: Unsplash by Maria Lupan

About This Quiz

Psychology says that we reach a generous age as we get older called generativity. As some of our most beloved baby boomers scale the mountain of age and wisdom, we've noticed that a lot of them have moved away from being in the public eye and straight into helping others. Throughout this quiz, you'll put together a team of baby boomer celebrities who wouldn't mind using their status to pull off the most glamorous and star-studded event in all the land! 

Charity events are a big to-do in Hollywood circles. If you're not on the list, you're not on the A-list. But all the boomers you get to choose from have already made their way through the complicated world of Tinseltown's charity circuit. In fact, they know enough about them to help you pull off the philanthropic event of the century! Your dream team is out to make a difference.

Once you've filled every position on your team, we'll know if you're closer in age to someone born at the start or the end of the generation. While age is just a number, your choices will show how many years you've had on the planet, getting others to do what you need them to do. Will we get your age right, or will you be forced to say, "OK, boomer?" Let's hit the red carpet and find out!

Oprah and Gayle Which one of these boomers would you want heading up your team?
Oliver Stone
John Travolta
Oprah Winfrey
Jodie Foster

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Bill Gates And who's going to look after your dream team's money?
Donald Trump would be a great treasurer.
Dolly Parton seems to have managed her money well.
Bill Gates gets my vote.
Let's see how Vanna White handles our budget.

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Roseanne Are you going to swap out Roseanne for a different funny baby boomer?
Whoopi Goldberg is a lot funnier.
I'm going to replace her with Weird Al Yankovic.
Arsenio Hall would be a great sub!
I'll keep Roseanne.

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Vanna White Who are you going to trust to send out the invitations to the big party?
Vanna White
Cybill Shepherd
Vanessa Williams
Daryl Hannah

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Elizabeth Warren and Steven Colbert Which politician do you want representing you in negotiations?
Al Franken
Elizabeth Warren
Al Gore
John Kasich

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Julian Lennon Bono wants to sit out for a while; who's going to replace him?
Courtney Love can handle it.
I think Julian Lennon learned enough from his dad to get the job done.
Bono is going to have to tough it out.
How about Annie Lennox? She's a much better singer.

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Madonna Are you gonna let Madonna or Alice Cooper deal with the team's entertainment?
Can I ask Olivia Newton-John to do it instead?
I'll stick with Madonna.
Alice Cooper throws my kind of parties!
Let's have Stevie Nicks do it.

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Tommy Hilfinger Which one of these boomer-era designers gets to create your uniforms?
Tommy Hilfiger
Gianni Versace
Cheryl Tiegs
Kathi Lee Gifford

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Maria Shriver 2 Will you allow Maria Shriver or Arnold Schwarzenegger to head up publicity?
I need Arnold on the field.
They're kind of a package deal.
I think Maria Shriver would do a better job.
They would be a great tag team!

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Crystal Gayle Which country singer would do a better job making fans smile?
Randy Travis is the man for the job!
I think Tanya Tucker could pull it off.
Everyone loves Crystal Gayle.
Without a doubt, Linda Ronstadt would nail it!

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Scott Hamilton Out of these baby boomer athletes, who would make the best team life coach?
Scott Hamilton would bring grace to that position.
We don't need an athlete for that when we have Al Sharpton.
Jimmy Connors would tell them like it is.
How about Nolan Ryan? He's great with that stuff.

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David Copperfield Whose creative mind do you want behind graphics and slogans?
Cheech Marin could suck the kids in.
They would pay attention to anything David Copperfield does.
Billy Ray Cyrus would be great at that stuff.
Have you seen George Bush's paintings? He could totally do it!

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Larry Csonka What famous football player gets to pump everyone up before the big day?
Doug Flutie
Boomer Esiason
Larry Csonka
I would have O.J. do it, but ... you know.

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Elton John Elton John wants to be on the team; what job are you going to give him?
He can be our spokesperson.
I really wish he could be a wardrobe consultant.
Elton would be a great manager.
Maybe he'll be happy just to sign autographs.

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Tom Cruise fix Who do you think will be your team's biggest diva?
Ted Bundy
Tom Cruise
Princess Diana
Sandy Duncan

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Geena Davis Demi Moore has asked to sit this one out. Who will fill her slot?
Brigette Nielsen is the logical choice.
I want to see how Geena Davis performs.
Carrie Fisher should've already been in the position.
That just leaves room for Sally Field.

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Amy Grant Which musical number is Paul Shaffer going to back up?
I hope it's Peter Gabriel.
I would love to hear Paul with Bruce Springsteen.
I haven't heard anything from Amy Grant in a while.
Let's slide Karen Carpenter into that position.

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Hillary Clinton Every team gets a legal consultant; who will you hire?
Kenneth Starr
Clarence Thomas
Hilary Clinton
Marcia Clark

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Dennis Rodman Will you let Fabio or Dennis Rodman be the face of the team?
I was hoping for someone a little more feminine like Bo Derek.
Fabio knows all about giving face.
I think Dennis Rodman would do a better job.
I really think Suzanna Summers should get the job.

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John Travolta What position do you have in mind for John Travolta?
He can be the choreographer.
Travolta would be a good secretary.
I'm putting him in charge of security.
I want him to do a duet with Olivia Newton-John.

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George Forman Would you rather have George Foreman or Richard Simmons deliver your sales pitch?
Can I have both?
I think George will do a better job.
Everyone loves Richard Simmons!
Lou Ferrigno should get the honor.

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Sarah, Duchess of York interview Who gets to be in charge of selling merchandise?
Sarah, Duchess of York
Christopher Reeve
Katie Couric
Ted Danson

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Laura Bush Which baby boomer celebrity are you putting in charge of food?
Jimmy Buffet knows how to party!
Laura Bush would make a lovely spread of food.
Marla Maples would get the job done.
I've heard that John Ritter was an excellent cook.

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Eddie Van Halen Are you going to let Gene Simmons or Eddie Van Halen sing the national anthem?
I didn't know that Eddie Van Halen can sing.
Gene would do a great job.
I think Whitney Houston should do it.
Anyone but Roseanne!

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Michael Jordan and Barack Obama Which of these baby boomers will you surprise with a lifetime achievement award?
Michael Jordan
Jon Bon Jovi
Tommy Lee Jones
Stephen King

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Steven Spielberg Who's going to be in charge of all the camera work?
David Lynch will do a great job!
I'm putting Steven Spielberg in charge of that.
Rob Reiner!
Let's go with Quentin Tarantino.

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Drew Carey Are you going to let Drew Carey emcee the event?
I think he'll be perfect!
Conan O'Brien would be funnier.
I'm going to have Alan Thicke do it.
Billy Crystal can handle it.

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Ted Danson Which celebrity will offer the closing speech?
Kevin Costner
Bill O'Reilly
Marie Osmond
Ted Danson

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Melanie Griffith Who do you think will be most likely to stick around for autographs?
David Copperfield loves doing that stuff.
I think Sissy Spacek will do it.
Melanie Griffith has already volunteered.
Bruce Willis

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Diane Keaton Jay Leno's agent won't let him attend. Who will you give his seat to instead?
Shelley Long
Tony Blair
Diane Keaton
Jeremy Irons

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