I am what they call a full 'One-Eighth'; one-eighth Chippewa. Those are my people.
— Darryl Whitefeather, "Josh Just Happens to Live Here"
Portrayed by Pete Gardner
Darryl Whitefeather is Rebecca Bunch's boss and the head of the law firm Whitefeather & Associates. He was born in Irvine, California and is proud of his 1/8 Chippewa heritage. Darryl is eager to identify himself as a Native-American despite that tenuous connection. He takes a somewhat parental role over his employees, particularly Paula Proctor whom he considers his best friend. Darryl got divorced from his wife Stacy and has a daughter named Madison with whom he shares custody. He has also recently discovered he is bi-sexual and has begun a relationship with Josh Wilson. His first appearance was in the Season One episode "Josh Just Happens to Live Here!". He is portrayed by actor Pete Gardner.
Now it's true I'm not gay...I Darryl Whitefeather like both sexes, I'm both-sexual! God, it feels so good just to say that out loud!
–Darryl, ""Josh and I Work a Case!"
In 2015, Darryl Whitefeather welcomed a former Manhattan attorney Rebecca Bunch to Whitefeather & Associates. She had been eager to relocate to West Covina and had asked to join his law firm. Darryl was happy to hire her not only because of her excellent resume but also since she was willing to take a substantial pay cut. She agreed to represent him in his divorce and got him an amicable shared custody settlement for his daughter Madison. With his divorce out of the way Darryl tried to move on and build new personal relationships. He attempted to socialize with a group of guys Rebecca had gotten acquainted with. This included a personal trainer he knew from a gym he frequented called Josh Wilson. After "White Josh" kissed him on the cheek Darryl found himself questioning his sexual orientation. After some soul searching he declared himself to be "both-sexual" and began a relationship with Wilson.
Towards the end of 2015, Darryl welcomed his latest hire Rebecca Bunch to his law firm Whitefeather & Associates. He was excited have an attorney with her impressive credentials at his firm and personally gave her a tour of the office. Darryl introduced her to the head paralegal Paula Proctor and Mrs.Hernandez the communications director. After showing Rebecca her office he asked her a personal favor. At the time Darryl was going through a divorce and needed a good lawyer to represent him. He told Rebecca his ex-wife Stacy had a smart Jewish attorney and thought he should have one himself. Rebecca told him she would think about it but also indicated she found the way he phrased his request a bit offensive ("Josh Just Happens to Live Here!").
Darryl went to the break room humming a Christmas carol and grabbed a Luna Bar from the cupboard. An annoyed Paula told him it wasn't Christmas and Darryl replied that he knew he just loved the song. He asked her where Rebecca was since they've been sitting together during break but Paula acted as if she didn't care. Darryl was happy Rebecca wasn't there since she usually gets to the lemon flavored bar before he does. Paula told Darryl the bars are meant for women since they contain menstrual blood. Darryl was skeptical and called the company's customer service line. After he finished talking to a representative he saw that Rebecca and Paula were hugging each other but when he tried to join in got rebuffed. He then told Paula he learned what she said wasn't true and left to finish the lunar bar elsewhere ("Josh's Girlfriend is Really Cool!").
Darryl was invited to Rebecca's housewarming party and he wound up being one of only a handful of people who showed up. When Paula arrived to help Rebecca out with the festivities he was talking to another guest named Brody about his disfigurement. They wound up in Rebecca's backyard playing piñata as Darryl was being taunted by Brody for not hitting the target. Another guest named Josh Chan took charge of the party and had everyone there pose for a group photo. It's then that the party kicked into high gear when Paula brought a Gamblers Anonymous support group. Darryl wound up having a great conversation who a lady who unbenowst to him gave him meth. Rebecca pointed this out to Darryl but he didn't believe it
("I Hope Josh Comes to My Party!").
Darryl is surprised when Rebecca agrees time his attorney for his divorce proceedings. At her suggestion he left Paula in charge of the office while he and Rebecca work on the case. He tries to explain to Rebecca just how much his daughter Madison means to him (♫ I Love My Daughter ♫). He and Rebecca interviewed Madison and learned that Darryl's ex-wife Stacy had been leaving thier daughter by herself to have trysts with her boss. Due to this evidence the judge awarded Darryl temporary full custody of Madison. At that emergency hearing, Darryl was shocked and saddened to learn of Stacy's infidelities during thier marriage. Later he was surprised and happy to learn that Stacy and Rebecca agreed to hammer out a fairer custody agreement. He and Stacy then accompanied Madison to a baseball game she was playing in ("Josh and I Are Good People!").
Excuse me everyone. Josh, I just want to thank you for including me in this stag party. I am just so excited...and as Rebecca's boss and mentor and White Josh's main squeeze I feel like I'm the marshmallow that's holding together this rice crispy treat.
–Darryl Whitefeather, "Can Josh Take A Leap of Faith?"
After going to Jayma Chan's wedding together Darryl and White Josh's relationship was continuing to go well. Things briefly hit a rough patch when they attended Electric Mesa together but it led to a serious dialogue about thier future together which strengthend their commitment to each other. He then officially introduced WhiJo to his daughter Madison and the two of them hit it off. At work Darryl encouraged and supported Paula who had decided to go to Law school despite her annoyance. He also intervened when Paula and her husband Scott were having marital difficulties and inadvertently helped them reconcile. Darryl also made a major business decision by selling half of his law firm to Nathaniel Plimpton. He came to regret his decision as Nathan became full owner of the firm and Darryl was essentially demoted. Eventually he began to bond with Nathan after several incidents involving a treadmill desk, flatulence and nap time. He and WhiJo attended the stag party of Josh Chan who got engaged to Rebecca. Darryl was bothered when he learned WhiJo didn't believe in the institution of marriage. Darryl eventually accepted WhiJo's beliefs but shocked his boyfriend by saying he wanted them to have a baby together.
Actor/comedian Michael McDonald of Mad TV fame was originally cast in the part of Darryl Whitefeather. He played the character in the Showtime Network ordered pilot episode. In a Scriptnotes podcast, show co-creator Aline Brosh McKenna stated that McDonald brought a "weird intensity" to Darryl that edged him out over the other actors who auditioned (this included his eventual replacement Pete Gardner). However, due to commitments McDonald had on another project he was unable to stay on the show when it was ultimately picked up by The CW. His scenes were later reshot with Gardner who delivered ad-libbed lines from McDonald that were added to the script.