|“||Wow! Look at my girl. All poofed up! Guess that makes me Poof Daddy!||”|
|— Jimmy to Tess|
He was portrayed by Mike Massimino.
Jimmy O'Malley cuts his final run of the week short, managing to return to Chicago in time to attend the annual George Washington Carver Community School Father Daughter Dance, and surprise his daughter, Tess. Arriving home at 352 Hauser Avenue, he simply parks his rig on the street. After changing into a suit, he steps across the hall to speak with his neighbor, Raven Baxter. The door is answered by Levi Grayson, as Raven is across the room, dressed as a man with a false bushy mustache. After the two friends share a hug, Raven explains that Devon is stranded at a nearby airport, and can't get into the city, and she was considering going to the dance in his place for their daughter Nia's sake. Jimmy is sorry that Devon won't be at the dance, and asks Raven to watch his truck parked outside. Raven asks how his rig handles snow, and before handing her the keys, Jimmy assures Raven it handles snow like a "twelve ton dream." Jimmy arrives at the dance and notices Tess and Nia at the DJ stand. Signaling Nia to keep quiet, Jimmy sneaks behind his daughter, and asks if they are taking requests. Tess turns around with a snarky retort, but is delighted and surprised to see her dad and jumps into his arms. After swinging Tess to stand on the floor, Jimmy tells her he couldn't let his little girl down and came to surprise her. Yet, Jimmy cannot resist pinching Tess' cheeks, much to her discomfort, but her father blames Tess, herself, for having such pinchable cheeks. Nia steps down to greet Mr. O'Malley, and after giving her a hug, he says that he is sorry Devon isn't there, but is happy to have two beautiful princesses to dance with. However, Jimmy tells the girls he needs to fuel up first, and heads for the refreshment tables, heeding the warning his daughter gives about avoiding dairy products. While preparing a plate of food, Jimmy takes the opportunity to subtly adjust the hair atop his head. Jimmy sits at a table to eat his food, and is soon joined by Tess now wearing Nia's dress. Jimmy is impressed, by how the "poofs" make his daughter appear, and dubs himself a "Poof Daddy." Tess teases her dad to talk less and dance more, but after watching him take a few steps, she reverses herself, telling him to talk more and dance less. The pair sit out the next dance, to sit and eat a bit, but are ready to resume, when the music starts again. Nia then approaches them, saying how good Tess looks. Tess agrees, stating that she thinks she really pulls the dress off. Nia then grasps Tess' wrist and leads her away, leaving Jimmy alone on the dance floor by himself. The girls return, a few minutes later, now dressed in their original clothes. The trio dance to the far side of the gym floor as Nia's brother, Booker, seems have involved himself, in some kind of drama in the center of the room. After they pose for their dance portrait, Tess then resumes her duties as the dance DJ. However, after Tess cues up the last song for the final dance of the evening, Jimmy is already on the floor, rose in hand, ready to share a last dance of the night, with his daughter Tess.
Tess reveals that her dad is "Chicago" Jimmy to the rest of the O'Malleys as it is a common name which includes her uncles "Ohio" Jimmy and "Long Island" Jimmy.
Smoky Flow (mentioned)
Reluctantly, Tess admits that her parents have been letting her stay at home on her own a lot more lately, due to Jimmy getting less trucking assignments, and as a result, Mrs. O'Malley has been volunteering to work double shifts at her hospital job, to make up for the lost income.
- He enjoys pinching Tess' cheeks, much to her embarrassment.
- He wears a toupee.
- Tess implies he is lactose intolerant.
- When in town, he has been known to drop off the kids at school with his rig.
- He is known as "Chicago" Jimmy among the O'Malleys, as Jimmy is a common name in the family.
- In Smoky Flow, Tess reveals that Jimmy has been getting less trucking assignments, and her mother now frequently works double shifts at her hospital job to make up for the lost income.
- He's the only one of Tess's parents to appear. Although her mother's hands were seen in "Head Over Wheels" handing Myra to Booker.
- In the original script for Oh Father, Where Art Thou?:
- Jimmy was described as "TESS' DAD, FUNNY, TEAMSTER-TYPE GUY, WEARING A FLANNEL SHIRT AND A CAP"
- It was the first time Levi met Mr. O'Malley.
- Raven offered to lend Jimmy the suit she was wearing.
- Raven and Jimmy simply switched keys, as he didn't want to drive his rig to school.
- Jimmy offered Raven as much chicken as she wanted off his truck.
- There was a running joke of Jimmy having one suit for all occasions, which he called his "wedding-funeral-baptism-first communion-graduation-daddy daughter dance" suit.
| The image gallery for Jimmy O'Malley may be viewed here.