Best of Chicago Advertising in 2023


The creative struggle — that ongoing battle to keep great advertising great from inception to production — is real.

Crafting advertising that not only captures attention, but also resonates with audiences on a deep level requires a unique blend of creativity, strategic thinking, and relentless perseverance.

Recognizing the arduous path that agencies tread especially in 2023, Reel Chicago proudly bestows the title of Creative Agency of the Year upon Chicago’s own Highdive Agency, a testament to their exceptional ability to navigate the creative struggle.

Creating great advertising is not for the faint of heart. It demands a constant dance between innovation and market relevance, pushing the boundaries while ensuring that the message remains authentic and impactful. Agencies face the challenge of capturing the ever-evolving zeitgeist, understanding the nuances of diverse audiences, and staying ahead of the curve in a landscape where attention spans are fleeting.

In the heart of Chicago, Highdive has emerged as a beacon of creativity, successfully navigating the tumultuous waters of the advertising industry. Their commitment to pushing creative boundaries while staying rooted in strategic thinking sets them apart in a landscape where mediocrity often prevails.

Their success is not solely based on the brilliance of individual campaigns but on a holistic approach to creativity and strategic thinking. Their work reflects a deep understanding of the brands they represent and an unwavering commitment to authenticity.

And they can be funny as hell. That’s why many of Highdive’s spots and campaigns fill our Top 10 of the Year below:

Reel Chicago’s Top 10 Advertising Campaigns

Jeep Electric Boogies its way into Super Bowl

Jeep’s Super Bowl one-minute commercial Electric Boogie celebrates the brand’s expansion of its electrified lineup across the world, taking the new interpretation of the iconic song into the future with the brand’s new generation of vehicles. 

The commercial created by Highdive, debuts today and features the brand’s hybrid electric plug-in vehicles Jeep Wrangler 4xe and Grand Cherokee 4xe with species from across the animal kingdom dancing along to the all-new “Electric Boogie” track. 

Ram explores premature electrification for Super Bowl

Ram unveiled its highly anticipated all-new Ram 1500 REV battery-electric truck for the first time today as part of the brand’s Big Game efforts. The commercial also signaled the official opening of customer reservations for a place in line to per-order the truck at

The 60-second commercial, “Premature Electrification,” was released early today across Ram’s social media channels. The spot featured Emmy-nominated actor Jason Jones (The Detour, The Flight Attendant, The Daily Show) as he addresses head-on some potential electrification anxieties that consumers may have about purchasing an all-electric vehicle, including range, power and payload. 

Highdive and Cutters team up for an epic Jersey Mike’s Big Game ad

In the online spot created and produced by the independent Chicago-based agency, Highdive, Danny Devito shares his thoughts for Jersey Mike’s eventual Big Game ad to help inspire viewers.

“Danny alludes to how he could wrestle a bear, he could be the voice of a talking sub, or even steal the crown jewels,” said Mark Gross, co-founder and co-chief creative officer at Highdive. “He also teases that he could ride a rocket to save the world from an asteroid with the same bear he wrestles. But for now, all of these are just ideas brewing in Danny’s head; a teaser of what could come to life, someday.”

NHL releases new Highdive creative for 2023 Stanley Cup Playoffs

Created by Highdive. each of the three spots Look UpFirst Kiss, and Built to Share, underscore the magic, thrills and emotions players and fans experience in the presence of the Stanley Cup.

First Kiss is from the perspective of winning Players in the euphoric moment and the tradition of kissing the Cup for the first time.

Look Up is a reminder of how young fans dream of hoisting the Cup and, for a select few, it turns into reality.

Built to Share highlights the Stanley Cup’s meaning and emotional connection with people around the world in its role as hockey’s greatest ambassador.

Havas creates funeral home in lobby to promote suicide prevention

Havas Chicago took a unique and thought-provoking approach to draw attention to this alarming statistic and inspire action during Suicide Prevention Awareness Week.

The agency launched a compelling and unconventional initiative by converting its front lobby into what they call the “11 Minutes Funeral Home.” This powerful activation is designed to shed light on the importance of recognizing signs of mental distress and encouraging meaningful conversations about suicide prevention.


Burrell makes life grander in Toyota’s Grand Highlander

Aptly titled “Life’s Grander in the Grand Highlander,” this campaign, created by Burrell aims to shine a spotlight on Toyota’s first-ever three-row SUV, emphasizing its spaciousness, design, and the impressive Hybrid MAX powertrain.

But that’s not all; what makes this campaign even more exciting is that it marks the commercial directorial debut of none other than Pretty Bird’s Kenya Barris, the creative genius behind the hit TV show Blackish.

Two captivating spots in this campaign stand out. The first spot, “Back There,” features playful kids enjoying the spacious backseat of the Grand Highlander. Mom puts a humorous and heartwarming twist on the classic phrase, “Don’t make me come back there!” It’s a delightful take on family dynamics during a road trip. 

Cottonelle reinvents down there care in FCB Chicago campaign

Cottonelle is dedicated to breaking barriers and challenging the toilet paper status quo by exploring real down-there issues in the FCB Chicago campaign.

Nearly half of consumers are dissatisfied with current toileting solutions because brands are solely focusing on the softness and strength of products instead of solving their real needs, including reducing odor, residue, excess moisture, skin irritation, and skin protection.

Cottonelle released four unconventional spots. The campaign aims to normalize the often-avoided “down there” conversation and give consumers the confidence to find solutions with Cottonelle’s suite of products, including bath tissue and flushable wipes.

Bear Naked Granola partners with Burnett for nude-friendly hikes

July 14th was National Nude Day in the United States and Bear Naked Granola, in collaboration with Leo Burnett Chicago and Gaia GPS from Outside, introduced an innovative and daring campaign.

The campaign aimed to make nude hiking more accessible by launching America’s first unofficial nude-friendly trail system.

For those who relish experiencing the beauty of nature in the buff, navigating the legal and cultural landscape can be a daunting task. Laws regarding nudity vary from place to place, and societal biases can create obstacles for nude hikers, figuratively and literally, leaving them feeling “lost in the woods.”

Bear Naked Granola

Andy Richter directs monsters, ghouls and villains for STORY

Director Andy Richter, and former Conan O’Brien sidekick, at STORY, teamed up with Quality Meats Creative, and 11 Dollar Bill to create three brilliantly funny spots for Regal Cinemas to drive home the point that movies are better seen at the theater.

Jimmy John’s redefines what MILF means

Jimmy John’s is tempting chocolate-lovers this Valentine’s Day with the release of a sweet new dessert, the Red Velvet Cookie, available for a limited time.

To honor the release of this sensational new treat, Jimmy John’s partnered with multi-platinum rapper, TikTok superstar and notorious fan of older women, Yung Gravy, to redefine the term “MILF” to “Moms I’d Like to FEED.”

Congratulations to Highdive and all of the other great Chicago agencies, production companies and post-houses fighting the good fight to get great creative out there. Looking forward to what you put out in 2024.

Tessa director Blaine Hogan goes intergenerational for Picklr

A heart-pounding new commercial for The Picklr, a rapidly expanding chain of indoor pickleball courts, is setting the stage for this emerging sport with a fresh, high-energy twist.

In “Winner Stays On!,” director Blaine Hogan of Tessa Films collaborates directly with The Picklr’s brand team to create a captivating anthem spot that is irresistibly fun.

ALSO READ: 2023 in Review: The Best Campaigns of the Year



Colin Costello is the West Coast Editor of Reel 360. Contact him at or follow him on Twitter at @colinthewriter1