Steve Carell
![Steve Carell](https://ew.com/thmb/ZPQuGaymvibNGV7vkSnMIVjzBfA=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/steve-carell-crazy-stupid-love-1-1378d9e6255042769f749b8eb8e3859d.jpg)
Decades into his career, Steve Carell joined Crazy, Stupid, Love. as Cal Weaver, a middle-aged man trying to find himself again after splitting from his wife. The future star got his start in the late '80s, appearing in commercials (such as the ad for Brown's Chicken shown above), and flexing his comedy chops as a part of The Second City.
Ryan Gosling
![Ryan Gosling](https://ew.com/thmb/GL2Y_iO2TBVFZKJjAsZoHXHxU_A=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/ryan-gosling-crazy-stupid-love-2-ecbc1577487d457dbd1c1e93699db412.jpg)
Ryan Gosling played Jacob in Crazy, Stupid, Love., a suave man who takes Cal under his wing and helps him in his transformation. The hunky actor made his on-screen debut years before preaching the gospel of being better than the Gap, getting an early start as a member of the Mickey Mouse Club (pictured above).
Julianne Moore
![Julianne Moore](https://ew.com/thmb/PExnSraWx_eydoStgyqhEZ-gJI0=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/julianne-moore-crazy-stupid-love-3-2d6820f312d34939b73345659a22ad04.jpg)
Julianne Moore found her spot in Crazy, Stupid, Love. as Emily Weaver, Cal's estranged wife. The actress earned her first on-screen credit decades prior, appearing in an episode of the soap opera The Edge of Night.
Emma Stone
![Emma Stone](https://ew.com/thmb/8at0yBrHedJtCw5yvstae1TPYro=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/emma-stone-crazy-stupid-love-4-5f55c327c9d14b418ec61d7ad3a13d35.jpg)
Years before she signed on to play Hannah, Cal's daughter and Jacob's love interest, Emma Stone was building up her résumé on the small screen. The star picked up one of her first credits for an episode of Malcolm in the Middle (pictured above).
Analeigh Tipton
![Analeigh Tipton](https://ew.com/thmb/YkgoUg7ygQoxW9aeGzauN3iC98o=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/analeigh-tipton-crazy-stupid-love-5-e17b2b16c8d5491a8aaa1f0cb4f68d05.jpg)
While Analeigh Tipton went on to be a successful actress, starring in Crazy, Stupid, Love. as high school student Jessica, she got her start as a contestant on America's Next Top Model in 2008 (pictured above).
Joey King
![Joey King](https://ew.com/thmb/IG-rowcwktgYmnzznuSGvvGwLLU=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/joey-king-crazy-stupid-love-6-3027c6ab8b8c471696c736e7b2337531.jpg)
Still early in her career at the time, Joey King signed on to play Molly Weaver, the daughter to Cal and Emily. The young star's first roles came a few years prior, including an uncredited turn in 2007's Reign Over Me (pictured above).
Jonah Bobo
![Jonah Bobo](https://ew.com/thmb/VPfSCFedGV160dcWhTl-0XJ2fr0=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/jonah-bobo-crazy-stupid-love-7-feede1d0d4954adca7edd36f0facd6ef.jpg)
Crazy, Stupid, Love. found its Robbie (the son to Cal and Emily) in Jonah Bobo. The young actor had a few roles to his name at the time, including an appearance in 2004's The Best Thief in the World (pictured above).
Marisa Tomei
![Marisa Tomei](https://ew.com/thmb/FQB5z-FabyLgdUaaH5JUtTSL_kI=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/marisa-tomei-crazy-stupid-love-8-69b92293e990408898368bceba38bb79.jpg)
Already an established star when she joined Crazy, Stupid, Love., Marisa Tomei played Kate, a teacher with whom Cal becomes involved. The actress earned one of her first on-screen credits in 1984, appearing in a handful of episodes of As the World Turns.
John Carroll Lynch
![John Carroll Lynch](https://ew.com/thmb/c1riALUgQfj1OyfBeizpNfS5fGE=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/john-carroll-lynch-crazy-stupid-love-12-2d3cfcaba58a45f3bbb8137ad41006e4.jpg)
John Carroll Lynch joined Crazy, Stupid, Love. as Bernie, Cal's estranged best friend and Jessica's father. Lynch made one of his first on-screen appearances decades prior, playing Norm Gunderson in Fargo.
Beth Littleford
![Beth Littleford](https://ew.com/thmb/B4J9b9E7bs2edBJHk4Zmd7dNTJw=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/beth-littleford-crazy-stupid-love-9-98269ef7eeaa4fa59f50944687e8eff4.jpg)
Beth Littleford appeared in Crazy, Stupid, Love. as Claire, Jessica's mother. One of the actress' earliest credits was thanks to Spin City, in which she played Deidre West for a handful of episodes.
Kevin Bacon
![Kevin Bacon](https://ew.com/thmb/0QmKOo6GOPcj6ZQIsuE9FMdG1IM=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/kevin-bacon-crazy-stupid-love-10-04dc85ee1a374f27a12909333b5123ca.jpg)
Kevin Bacon lent his star power to Crazy, Stupid, Love. as David Lindhagen, Emily's man on the side. The actor landed his first big-screen role in the '70s, playing Chip Diller in Animal House (pictured above).
Josh Groban
![Josh Groban](https://ew.com/thmb/q8pGIJ9aCqc93R53aCLS2mQWxtc=/1500x0/filters:no_upscale():max_bytes(150000):strip_icc()/josh-groban-crazy-stupid-love-11-05a4bd154547473380dd952aa351d010.jpg)
Known best for his recording career, Josh Groban popped up in Crazy, Stupid, Love. as Hannah's disappointing boyfriend Richard. He kicked off his singing career as a teen, making appearances at local shows.