Simon put forth his best effort to persuade Kelly Clarkson to record a commercial. He outlined the details for the client, hoping her voice would be the perfect fit.

Simon’s encouragement for Sydney to spearhead the advertising campaign for Windy City Coffee proves to be a recipe for chaos. Separately, Zach finds himself consumed by envy when Simon assigns Andrew the responsibility of caring for a famil…

The client pitch cast an unfavorable shadow on the relationship between Simon and his daughter, Sydney. Determined to atone for the sting of her childhood, Simon resolves to patiently re-teach Sydney the art of driving. Separately, Andrew’s…

The breakfast burrito campaign remained a distant thought, perpetually deferred. Instead of brainstorming slogans or sketching visuals, the group settled into a comfortable inertia, postponing any actual work.

The three men – Sydney, Zach, and Simon – found themselves in a subtle contest, each vying to capture the interest of a discerning client with a global perspective.

A ripple of surprise went through Sydney when she learned her long-held high school crush had been nominated for a significant award. The news carried a sharp, unexpected twist: the same award was being bestowed upon her father, placing the…

Josh Groban, a former colleague of Sydney's, has penned a song in her honor. Meanwhile, Simon grapples with a difficult vocal passage.

Disagreement invariably led to Brad Garrett, Simon and Sydney’s partner, demanding that Simon relinquish his initial client.

The outcome of the annual accounts versus creative sixteen-inch softball game carries significant weight, potentially impacting someone's position. The details surrounding Simon’s most recent victory may finally come to light.

A coveted client threatens to expose the fundamental differences between Gordon and Simon, their ambitions colliding in the pursuit of a significant win. Meanwhile, Lauren finds herself unexpectedly ensnared in a predicament involving a bra…

The arrival of a privileged young woman, the spoiled daughter of a prominent client, as the newest intern at Roberts and Roberts stirs up old anxieties within Syndey.

A clerical error, a tangle of misplaced documents, led Sydney down an unexpected path. The resulting confusion, however, unlocked something within her – an intense fascination with a video game that quickly blossomed into an all-consuming o…

As a wave of influenza swept through the office, leaving colleagues incapacitated, Simon entrusted Lauren with a high-stakes client grappling with a public relations crisis.

Following a disheartening loss in a creativity contest, Andrew and Zach endeavor to rekindle Simon's inspiration. Meanwhile, Sydney harbors a concern that her burgeoning affection for a feline companion might detract from her connections wi…

Simon found himself tasked with delivering a eulogy for a jingle writer, a man whose personal qualities hadn't endeared him to many. The assignment felt, to Simon, like an unusual burden. He considered the man’s life, a curious tapestry wov…

Simon volunteered to orchestrate a bar mitzvah for a client’s son, but the carefully laid plans began to unravel when Zach encountered a former relationship.

Simon finds himself driven to meddle in Sydney’s burgeoning romance, a yearning for grandchildren outweighing all caution. Meanwhile, Andrew and Zach navigate their own paths to connection, each seeking a partner with differing approaches.

The boisterous energy of Andrew’s sisters filled the office as they arrived for a St. Patrick’s Day celebration – an occasion that consistently ranked as Simon’s least favorite.

Attempting to emulate Simon's confident demeanor, Zach delivers ambitious pronouncements during the pitch, needing to secure Brad Paisley's participation in a jingle penned by Danny Chase.

The dissolution of Gordon and his partner left Simon profoundly disheartened, fostering a deep disillusionment within him regarding matters of the heart.

Driven to avert the library's closure, the team explored unconventional solutions.

When a corporation makes a bid to acquire the firm, Simon finds himself subject to a rather pointed authority: his former wife. She holds the deciding power in the matter.