Dennis Rodman is a dichotomy if there ever was such a personification of one in NBA history. He is still hailed as arguably the greatest defensive player to ever play the sport, but for a number of years, his eccentric style was almost too eccentric for a '90s crowd to give him the credit he deserves.
Though his appearance probably fits right at home with the average 2019 millennial, the way he dressed, pierced his face, and dyed his hair (along with many of the comments he made regarding his sexuality) was considered weird to those in the '90s not used to seeing stuff like that.
But stuff like that is exactly what helped Rodman stand out among the NBA and helped him reach celebrity status within pop culture to reach an audience beyond just basketball fans. We are positive that given his success, Rodman probably has few regrets regarding his approach to life, but he might regret a few of the following pictures.
20 His Fight with Alonzo Mourning
Dennis Rodman was no stranger to using his many eccentricities to get in the head of his opponents. Alonzo Mourning was his target during a game against Miami Heat. Mind games must have gotten to Mourning's head since while attempting a rebound, Mourning fell on Rodman and while on the ground, put Rodman in a headlock and kicked at him.
19 Tussle with Frank Brickowski
Another example of Rodman's mind games on the court being on full display was in Game Three of the 1996 NBA Finals against the Seattle SuperSonics. This time, his target was Frank Brickowski. The whole game, Brickowski was visibly irritated by Rodman laughing and staring at him while locking down his offense. He got his payback by "accidentally" elbowing Rodman in the face.
18 His Sports Illustrated Cover
As mentioned earlier, a staple of Dennis Rodman's career was the fact that he dressed and acted so eccentric. A prime example was his extremely eccentric and infamous 1995 Sports Illustrated cover. Since he's toned down those eccentrics in recent years, he may want to leave this cover in the past.
17 His Meeting with Kim Jong Un
This is just one of many meetings that Dennis Rodman has had with his good ole pal Kim Jong Un. However, given the controversy he has suffered for befriending North Korea's Supreme Leader and how uncomfortable he often looks when explaining their friendship in interviews, like the one with Stephen Colbert, Rodman probably hopes folks don't see photos like this.
16 When He Married Himself
In one of Dennis Rodman's wackier moments, in 1996, to promote the release of his new book Bad As I Wanna Be, he put on a wedding dress - tailored with makeup and a wig ensemble - to marry himself. He even arraigned an entire wedding for himself and declared himself bisexual in the process.
15 His Infamous Interview
Dennis Rodman grew some negative press during an eccentric interview with Chris Cuomo where he went on a rant via satellite where he went on an angry rant. Considering Rodman went on to make a statement - released by his publicist Jules Feiler - apologizing for the rant, explaining he had been stressed out and drinking beforehand, Rodman likely regrets the whole thing.
14 When He Wrestled with Hulk Hogan
Dennis Rodman has always been an unapologetic wrestling fan. So much so that back in 1997, he wrestled alongside Hulk Hogan and became an official member of Hogan's bad guy group, the New World Order. Rodman went on to main event WCW's Bash at the Beach Pay-Per-View two years in a row tag-teaming with Hogan, once wrestling fellow NBA star Karl Malone.
13 Crashing His Ex's Party
In 2014, TMZ reported that Carmen Electra co-hosted a Fright Night Halloween Party in Florida, which is apropos given the horror story that she ran into her ex-husband Dennis Rodman at the party. A pic surfaced of the two locking eyes where Electra did not look too happy, but she later confirmed to Huffington Post that the two had a "nice" time catching up.
12 Better Times with His Ex
Even before he divorced from Carmen Electra, their happy union did not always suggest the best of times between these two. Like in this photo where Dennis Rodman is getting his cheeks squeezed like an infant by who at the time was his better half. Probably not something he would've wanted captured on camera.
11 His Hall of Fame Induction
A key point of his recent ESPN documentary was his Hall of Fame induction speech, where he apologized for being an absentee father to his kids and one of his ex-wives. He promised to be a better father and be around more often, but in a follow-up interview ESPN did for the doc, said ex-wife admitted nothing changed after his speech.
10 When He Kicked the Cameraman
In one of his more volatile moments on the basketball court, after falling to the ground during a 1997 basketball game, Rodman - out of frustration - kicked the cameraman he fell next to squarely between the legs. The poor guy was sprawled out in pain and had to be carried out on a stretcher.
9 Him and His Other Ex, Madonna
It is rare that Dennis Rodman speaks too fondly of his ex, Madonna. On numerous occasions (most recently during his recent ESPN 30 for 30 documentary), Rodman has said that they broke up because she wanted children with him, but he did not. Given how they broke up and how he speaks of her, he might not look fondly at any of their pics together.
Dennis Rodman cries a lot. One of his more recent cries came during a 2018 interview on CNN with Chris Cuomo, four years after their aforementioned infamous interview. While reflecting on the summit between the two higher-ups, Rodman was brought to endless tears.
7 When He Dressed in Drag
Dennis Rodman's fashion sense always bordered on androgyny and confusing people on his gender and sexuality. Here, he just went all out there by donning a classic, applaudable drag look with makeup and a suit. We wonder how he feels about this look now as he's noticeably and drastically toned down in favor of wearing strictly masculine clothes.
6 This Tanktop Look
To his credit, Dennis Rodman was typically able to rock his androgynous fashion style with a sense of impressive style and grace. Keyword: typically. Not every fashion choice Dennis Rodman made over the years was an impressive one. Exhibit A: this tragic excuse for a tank top that is barely hanging by a thread.
5 KISS Cosplay, while Gene Simmons is Unimpressed
In one of his memorable dress-up routines, Dennis Rodman donned the always instantly recognizable KISS makeup when meeting up with the band's former frontman, Gene Simmons. We are not sure if Simmons is just trying to look cool and stoic in their pic, or if he's unimpressed by Rodman's get-up. It might be both.
4 Looking Like a Hot Mess
Readers can say what they will about how Rodman dressed up and wore makeup, but he did so with so much style and glamour that it was hard to criticize him too hardly. This look, however, just looks like a hot mess. Glitter is just chaotically smeared onto his face with no pizzaz or allure like he used to have.
3 Out-Weirding Eric Andre on His Show
The Eric Andre Show has become famous for being a show where unsuspecting celebrity guests (thinking they are coming on to a real talk show) come on get asked outrageous questions and get weirded out by odd things happening on set. Rodman was one of the rare guests not weirded out and actually played along with the weirdness. Probably because he's weird himself.
2 Getting Dropped by Karl Malone
In a bizarre incident during a 1998 NBA Finals game between the Chicago Bulls and the Utah Jazz, Malone fell on top of Rodman. When both men tried to get up, they kept falling down whilst tripping over each other's legs. When Malone finally got to his feet, he unintentionally elbowed Rodman in the face. How embarrassing, especially for Rodman.
1 Kissing the Flight Attendant
In 2010, while boarding a flight from Madrid to Miami, Dennis Rodman took a picture with a flight attendant (who we have to assume was a fan of the man) during which he planted a kiss on his cheek. 10 years later, since Rodman has toned down his wackiness, he might wish this pic never went viral.
sources: tmz.com, huffpost.com