Shyer (along with Harvey Miller and--for the first time--Nancy Meyers) ventured into producing with "Private Benjamin" (1980), a bubbly money-maker starring Goldie Hawn as a suburban princess who joins the army. Shyer's directorial debut, "Irreconcilable Differences" (1984), displayed what was becoming his trademark style: adult comedies revolving around everyday middle-class life and "family values", with the characters in exaggerated familial situations. In the instance of "Irreconcilable Differences" (which he also co-produced and -wrote), Drew Barrymore played a painfully precocious kid who sued her parents for divorce. Shyer's "Baby Boom" (1987, which he also co-wrote with Meyers) featured Diane Keaton playing a yuppie who, sick of the urban life, takes to the hills of Vermont with her adopted infant on her arm. The film was an enormous success and led to a TV spin-off (NBC, 1988-89). Shyer and Meyers co-produced this as well, and Shyer wrote and directed the premiere episode.
"Father of the Bride" (1991, co-produced and -written with Meyers) was a remake of the 1950 chestnut, starring Steve Martin struggling with the age-old ritual of giving away his daughter. Shyer also directed and co-wrote (with Meyers) the 1995 sequel, "Father of the Bride Part II". Shyer's next two films did not fare well with either audiences or critics: he wrote (with Meyers and five others) the screwball comedy "Once Upon a Crime" (1992). He directed and co-wrote (with Meyers) "I Love Trouble" (1994), a bit of a departure in that it was not as suburban, starring Julia Roberts and Nick Nolte as two rival reporters who fall in love while researching a political cover-up. He next adapted and updated the screenplay for Disney's "The Parent Trap" for the 1998 sequel starring Lindsay Lohan in the dual Haley Mills roles and Dennis Quaid and Natasha Richardson as the befuddled divorced parents for whom the twins play Cupid, with Meyers directing. Their professional collaboration worked magic again to create a modest hit, but ironically Meyers and Shyers' personal relationship ended at the same time, with the couple's separation in 1998. After an extended hiatus, Shyer then assumed the director's chair--but not the writing chores--for "The Affair of the Necklace" (2001), a film set in pre-Revolutionary France in which a young aristocratic woman (Hilary Swank) left penniless by the political unrest in the country, must avenge her family's fall from grace by scheming to steal a priceless necklace. The tale of intrigue failed to prove intriguing to filmgoers, however, providing Shyer with a rare flop. Shyer then returned to the remake well that had served him famously in the 1990s, adapting the 1966 British cult classic "Alfie" with Jude Law in the womanizing role made famous by Michael Caine.