5 “Homer and Ned’s Hail Mary Pass” (2005) – Tom Brady
4 “Barting Over” (2003) – Tony Hawk
After Bart emancipates himself from the family and moves out on his own, Homer desperately tries to figure out a way to win back his son’s love. To do so, he pleads with Bart’s new neighbor, Tony Hawk, to let him beat him in a skateboarding competition. Tony sympathizes and offers Homer a skateboard that will help him look like a pro, calling it “the ultimate in poser technology.” What ensues is an epic, mid-air, Crouching Tiger Hidden Dragon-esque skateboard fight where Homer fells the mighty Tony Hawk. Tony then graciously offers Homer some parenting advice in unintelligible skater lingo, and Homer vows never to mistreat Bart again.
3 “Brother’s Little Helper” (1999) – Mark McGwire
When Bart is diagnosed with ADD and forced onto medication, he immediately becomes a model son and student. The one side effect however, is an extreme case of paranoia about being monitored by Major League Baseball (gotta have that express written consent!). When the doctors wean Bart off the drug, he downs a handful of pills, steals an army tank, and shoots down an MLB satellite. And that’s when Big Mac inexplicably shows up. McGwire offers to tell them all the terrifying truth of why they’re being spied on, or to hit a few dingers! He blasts a ball into the stratosphere then deftly steals the personal data from the satellite with a classic Simpsons “Yoink!”
2 “Bart Star” (1997) – Joe Namath
Maybe Joe Namath will never do anything as funny as the time he drunkenly hit on ESPN’s Suzy Kolber on the sidelines, but his appearance on the Simpsons was a close second. In the episode “Bart Star,” Homer takes over coaching duties of the local pee-wee football team and immediately yanks star quarterback Nelson, throwing a reluctant Bart into his spot. Fate seems to smile on Bart though when Joe Namath’s car breaks down outside the house, but instead of offering sage-like advice on quarterbacking, Joe just rambles on about the dangers of vehicle vapor lock. It’s completely nonsensical and yet hilarious, not unlike drunk Joe Namath in real life.
1 “Homer at the Bat” (1992) – Roger Clemens, Steve Sax, Mike Sciosca, Don Mattingly, Darryl Strawberry, Wade Boggs, Ken Griffey Jr. and Jose Canseco
Not only was this episode the best that featured pro athletes, it was also easily one of the greatest Simpsons episodes of all time. In “Homer at the Bat,” Mr. Burns hires pro baseball players to work at the plant in order to win a softball game against a rival. What ensues is comedic gold. Ken Griffey Jr.’s head grows to a freakish size thanks to his addiction to nerve tonic. Mike Scioscia is a model employee but quickly contracts radiation poisoning. Steve Sax is arrested for multiple homicide. Darryl Strawberry shows a softer side when Bart’s taunts make him cry. And Don Mattingly is continually reamed out by Mr. Burns for his damn hippie sideburns. In short, if you haven’t seen this episode, drop what you’re doing, quit your job if you have to, and just go watch it.