21 best sports books of the 21st century: a comprehensive list

Deep dives into the Chicago Bears, the original Dream Team, and the New York Yankees for lovers of sports literature top our list.

Do you want to read about the Dream Team? Of course you do! / USA TODAY via Imagn Content Services,

Not only are we sports writers. We’re also sports readers.

Being sports readers, we’re well aware that the vast majority of sports book “best of” lists that populate the interwebs include David Halberstam’s brilliant look at 1970s basketball, The Breaks of the Game; Jim Bouton’s hilarious insider baseball diary Ball Four, and something like 291 of Roger Angell’s baseball studies, all of which are ridiculously good.

Few of these lists, however, give significant love to books that were published in or after the year 2000. But that ends here.

Since we like numerical symmetry, here are 21 of the finest sports books that dropped in the 21st Century. And as we don’t want to play favorites, the list is alphabetical by author.

Wheelmen: Lance Armstrong, the Tour de France, and the Greatest Sports Conspiracy Ever

Reed Albergotti & Vanessa O’Connell

Once the whole Lance Armstrong doping mess calmed down, it was inevitable that both dialed-in sportswriters and hardcore investigative reporters would bang out book-length studies of the disgraced cyclist. Former Wall Street Journal sportswriter Albergotti’s and Reuters’ Global Industry editor O’Connell’s version of the Armstrong tale is the most readable and best-sourced of the bunch. In a weird way, they made Armstrong’s rise and fall, well, kinda fun to read about, which is eminently impressive.

Monsters: The 1985 Chicago Bears and the Wild Heart of Football

Rich Cohen

A lovely combination of memoir and historical study, lifelong Bears nut Cohen relates the gripping story of the only Monsters of the Midway squad to win a Super Bowl, while blending in details of his fandom in a manner that makes you want to invite him over to watch Red Zone every Sunday. Props to Rich for landing interviews with numerous members of the team, the most notable being a touching afternoon spent with the Bears’ punky QB, Jim McMahon.

Every Time I Talk to Liston: A Novel

Brian DeVido

Most of these sorts of lists have an entry or two where you’re like, “Um, never heard of that one,” and this cool novel is it. The deep cut piece of fiction comes from the pen of a former Virginia Golden Gloves heavyweight champ, so it’s little wonder that DeVido’s debut — the story of a troubled boxer and his up-and-coming manager — feels so damn real. His love for Sonny Liston adds a layer of pathos that one wouldn’t expect from boxing fiction.

Ali: A Life

Jonathan Eig

Joyce Carol Oates is a way better writer than any of us, so we’ll pull some fantastic words from her New York Times review of Eig’s modern classic: “Much in its pages will be familiar to those with some knowledge of boxing but even the familiar may be glimpsed from a new perspective in Eig's fluent prose; for pages in succession its narrative reads like a novel — a suspenseful novel with a cast of vivid characters who prevail through decades and who help to define the singular individual who was both a brilliantly innovative, incomparably charismatic heavyweight boxer and a public figure whose iconic significance shifted radically through the decades as in an unlikely fairy tale in which the most despised athlete in American history becomes, by the 21st century, the most beloved athlete in American history.”

Big Hair and Plastic Grass: A Funky Ride Through Baseball and America in the Swinging ‘70s

Dan Epstein

In terms of age demographic, our team here is all over the map, so this title from a colorful pop culture writer was fantastic for us in that the depiction of baseball’s 1970’s-era weirdness was a nostalgic look back for the old dudes, and an enriching historical study for the young dudes. The fact that Mark Fidrych is on the cover takes it over the edge.

A Few Seconds of Panic: A Sportswriter Plays in the NFL

Stefan Fatsis

A criminally underknown memoir, Fatsis’ tale of his journey to become a professional NFL kicker at the age of, um, fortysomething is the modern version of George Plimpton’s 1966 football literature classic, Paper Lion. The former Wall Street Journal sports scribe breaks down the kicking process, while bringing us inside the Denver Broncos’ locker room, a locker room that included a snarky Jay Cutler, a boisterous Jake Plummer, and an obnoxious Todd Sauerbrun. Considering the tight-lip-eness of today’s NFL, you’d be hard-pressed to find a more intimate look at The Shield.

K: A History of Baseball in Ten Pitches

Tyler Kepner

Kepner’s subtitle took cojones. Think about it: Baseball’s century-plus story is so rich and detailed that claiming you can tell its history via sliders and change ups is quite the brag. But the veteran baseball writer — whose work has been seen in the New York Times and The Athletic — pulls it off, utilizing Bob Gibson, Steve Carlton, Nolan Ryan, Greg Maddux, Mariano Rivera, and Clayton Kershaw as case studies. It sounds pedantic. It’s not.

Big Game: The NFL in Dangerous Times

Mark Lebovich

A political writer by trade, Lebovich gushes about his New England Patriots in a charming manner that would have your prototypical Masshole Pats fan screaming, “Ya too @&%#ing nice, Leebs!!!” But for non-Pats people (which is pretty much every football viewer outside of the Bay State) the 400 pages spent with Tom Brady, Bill Belichik, et al isn’t just tolerable — it’s fun. The fact that Lebovich makes Brady seem like a normal, down-to-earth fella is a feat in and of itself.

Dream Team: How Michael, Magic, Larry, Charles, and the Greatest Team of All Time Conquered the World and Changed the Game of Basketball Forever

Jack McCallum

These kinds of books are all about access, and the former Sports Illustrated staffer had plenty of it, landing quality time with most of the 1992 Olympic hoops roster. This allowed him to deliver quality reportage on the team’s off-court fun, the incessant insults (we’re talking to you, Michael Jordan, Charles Barkley, and Larry Bird), and the legendary Dream Team intersquad practice tilt that, in terms of actual basketball, was far more interesting than anything we saw at the Games.

Foul Lines: A Pro Basketball Novel

Jack McCallum & Jon Wertheim

Sports novels are very hit and very miss; here, McCallum and his former Sports Illustrated partner-in-crime hit, and hit hard. Admittedly, the premise is kind of ridiculous — a veteran All-Star shooting guard from a professional basketball team hides from the law after a hit-and-run car wreck, all while engaging in a will-they-won’t-they dance with a local paper’s new female beat reporter — but the authors brought their knowledge of NBA absurdity to the table, making for a farcical blast.

Sweetness: The Enigmatic Life of Walter Payton

Jeff Pearlman

Here, we begin the Jeff Pearlman portion of our program, a portion that would’ve been even larger had this article been, like, eight entries longer. As it is, we’re pulling three titles from Jeff’s impressive canon, this first one being his brilliant look at the legendary Bears’ running back. In this lush biography, Pearlman details Payton’s numerous physical and mental issues, giving us a surprising portrait of a Hall of Famer who many of us thought was nearly perfect.

Showtime: Magic, Kareem, Riley, and the Los Angeles Lakers Dynasty of the 1980s

Jeff Pearlman

If you’re not familiar with Pearlman — but are familiar with the HBO dramedy Winning Time: The Rise of the Laker Dynasty — this is the ideal place to meet this bestselling scribe. The author’s ability to fully depict the diverse, fascinating characters that made the Lake Show of the ‘80s must-see-TV is impressive as hell, and few wordsmiths could pull it off with such aplomb and charm.

Three-Ring Circus: Kobe, Shaq, Phil, and the Crazy Years of the Lakers Dynasty

Jeff Pearlman

The abovementioned Showtime clocks in at 496 pages. Three-Ring Circus runs 448 pages. Some quick addition tells us that Pearlman needed 944 pages to tell the stories of the mighty modern Lakers. Seems long, right? Okay, 944 pages is long, but it doesn’t feel long — which is why you should read these titles back-to-back, just like we did. (Note: The depiction of Kobe Bryant and Shaquille O’Neal’s tumultuous relationship is straight-up gripping.)

Stretch: The Unlikely Making of a Yoga Dude

Neal Pollack

Is yoga a sport? It’s not competitive, but it makes one sweat, so for the sake of this article, sure, let’s go ahead and call it a sport. An acclaimed satirist and novelist, Pollack doesn’t just goof around about his induction into the world of yoga, but he delves into the practice’s history and what the contemporary yoga scene looked like, circa 2010. And the section on “yoga farts” is worth the price of admission.

The Baseball 100

Joe Posnanski

A former senior writer at Sports Illustrated, Posnanski’s epic is simultaneously informative and touching, as he spends a goodly number of pages discussing baseball’s impact on his family. And his in-depth look at the greats of the Negro League is as good as it gets.

The Silver Linings Playbook: A Novel

Matthew Quick

Quick is one of the kings of the feel-good novel, and this story of a troubled high school teacher attempting to navigate his dysfunctional family, a painful divorce, and a mercurial love interest  — all while trying to keep up with his beloved Philadelphia Eagles — begins in a dark place. But come the third act, we defy you to keep your tear ducts under control. And FWIW, the movie version of Silver Linings is pretty darn good.

The Book of Basketball

Bill Simmons

If this list was a best-to-less-best ranking, Simmons’ 700-plus-page door-stopper might be right up top. An insanely detailed book that, believe it or not, is eminently re-readable, Bill’s breakdown of his love for the Celtics, the Bill Russell/Wilt Chamberlain debate, and the NBA’s greatest players is filled with relevant humor, hot takes galore, and awesome footnotes. ESPN Books dropped an updated version a few years after initial publication; it might be time for another.

Rope Burns: Stories From the Corner

F.X. Toole

There’s something about quality boxing fiction that’s…special. Toole’s astounding short story collection is beyond special — it’s a timeless classic. The pseudonym of former boxer and trainer Jerry Boyd, Toole introduces the reader to heavyweight champs, unscrupulous middleweights, and gun-toting gangsters. But perhaps the most intriguing story is “Million Dollar Baby,” a tragic tale of a gritty female boxer that was adapted into potentially the greates fight movie of all time, Rocky notwithstanding.

The Yankee Years

Joe Torre & Tom Verducci

Remember when Joe Torre was one of the most beloved managers in baseball? If you don’t, take a gander at his memoir of the memorable New York Yankees squads of the late-’90s and early-’00s. With a cast of characters featuring Derek Jeter, Bernie Williams, and Daryl Strawberry, Torre’s surprisingly honest telling of the team’s tale is fascinating, even for non-Yankee fans…of which there are a whole lot.

Fantasyland: A Season on Baseball’s Lunatic Fringe

Sam Walker

Can’t find my copy, but pound-for-pound this is my favorite baseball book ever. And it’s about fantasy baseball. Fantasyland by Sam Walker. pic.twitter.com/vVyx3tjWSK

— Brandon Walker (@BFW) March 28, 2023

We’d love to see more titles about fantasy sports on the shelves of our local book-a-torium. Thing is, who wants to read about somebody else’s league? Nobody, that’s who…that is, unless you’re plowing through a tome by a Wall Street Journal senior writer by the name of Sam Walker. In a Quixotic endeavor, Sam hires a young fantasy expert named Nando Di Fino (you might know of him) and a NASA scientist — that’s right, a NASA scientist — to help him win the legendary Tout Wars fantasy baseball league. Spoiler alert: Despite his Moneyball approach to fantasy, Walker didn’t bring home the hardware, but his trip through, yes, fantasyland is both illuminating and uproarious.