Simon must pull out all the stops and convince Grammy Award winner Kelly Clarkson to record a new twist on a classic advertising jingle for their biggest client.
When Simon encourages Sydney to take the lead on an ad campaign for Windy City Coffee, disaster ensues. Meanwhile, Zach is jealous when Simon tasks Andrew with taking care of a family of ducklings.
When a client pitch shines a negative light on Simon and Sydney's father-daughter relationship, Simon is determined to make up for all of Sydney's bad childhood memories by re-teaching her how to drive. Meanwhile, Andrew's confidence suffers when Lauren tells him that he is Zach's suckerfish.
While trying to brainstorm ideas for an ad campaign for a breakfast burrito, the gang procrastinates and delves into each other's personal lives.
When a worldly client, Helena, comes to town, Sydney, Zach and Simon each compete for her attention, but when things turn to a sexual nature, they realize they may know too much about each other.
When Simon is nominated for the prestigious Impact Award for Advertiser of the Year, Sydney is surprised to find that her high school crush is in direct competition for the award against her father.
An infatuated ex-co-worker of Sydney's writes a stalker-ish song about her. Meanwhile, Simon struggles to pitch the Australian Tourism Board, the location of his final bender.
Simon is intent to make things right when his partner, Gordon Lewis, forces him to give up his very first client when it conflicts with another account.
Someone's job is on the line at the annual Accounts vs. Creatives 16-inch softball game, and the truth about Simon's last epic win threatens to surface.
While Simon and Gordon disagree on compromising their values to land a lucrative client, Lauren gets stuck in the multi-million dollar Victoria's Secret Fantasy Bra.
Sydney's insecurities about how she is perceived resurface when the bratty daughter of an important client becomes their intern.
When Simon mixes up the assignments in the office, he puts Sydney on an account for a video game that she becomes addicted to winning.
Simon gives Lauren a chance to work with a big client facing a PR disaster when the rest of the office comes down with the flu.
When the agency's new research analyst defeats Simon in a creativity contest, Zach and Andrew work together to help Simon get his groove back. Meanwhile, Sydney worries that her new attachment to a cat will ruin her chances with future human relationships.
Woman asks Simon to eulogize her deceased father, a jingle writer who was not a well-liked man.
Simon offers to throw a client's son's Bar Mitzvah, but Zach's run-in with the only woman he's ever loved may upend the festivities.
Simon's desperation for grandchildren forces him to interfere with Sydney's new relationship. Meanwhile, Zach and Andrew try working with other partners.
Simon's hatred for all things related to St. Patrick's Day is exacerbated when Andrew's rowdy and spirited sisters descend on the office to celebrate the holiday.
Trying to channel Simon, Zach overpromises on a pitch and must get Brad Paisley to sing a jingle written by Danny Chase.
Simon's promising new relationship is tested when he becomes disillusioned with love after Gordon and his partner break up.
Simon and the team try an out-of-the-box idea in order to save a library from being shut down, and Gordon literally becomes the unwilling poster boy for the campaign.
When a corporation wants to buy out Lewis, Roberts+Roberts, Gordon calls in the board to vote, and Simon's ex-wife and Sydney's mom has the final say.
