Inside Digger's Acting Debut
You might remember us telling you Thursday about Digger Phelps' off-off-off-off-Broadway debut. Well, a Deadspin reader was in the audience Friday night, and files a full report.
Enjoy.
No Harry Potter kid. No tie-lighters. None of the phony Al-Gore-like gesticulations we've come to love to hate.
And in spite of Will's promising teaser Thursday about the play "Love Letters," its star, ESPN's own Digger Phelps, did not get naked.
Forty bucks in New York City's theater district doesn't go that far.
(Though, with the stagehands' strike here closing a slew of productions, my ticket money got me a lot more than those poor schmuck tourists who were forced to go to MoMA, god forbid.)
"Love Letters" wasn't the sort of thing you'd imagine seeing Phelps in. First off, "LL" is spare and understated - not exactly the profile of an ex-coach-turned-talking-head. The set was two desks with chairs (not a Hi-Liter in sight), and the script is basically two people reading one another their life-long correspondence.
Also, Phelps' character, Andy Ladd, is a dorky do-gooder who ends up a tightly wound U.S. senator. He enjoys writing letters - it's the only way he can express his feelings.To give you some perspective, the character has been portrayed in the past by Christopher Reeve and William Hurt.
Phelps' co-star was Cindy Williams. Please. Not that Cindy Williams. This Cindy Williams is a TV news anchor, though she does a passing Kathleen Turner. She's from Portland, Maine, not far from the Bush family's Kenne-bunker. Which explains how Phelps, an appointee to GHW Bush's administration as well as a politician wannabe, started vacationing in the area. Once there, for whatever reason, Phelps got involved in community theater, and starred in a couple local productions of "Love Letters." (Maybe he figured out it would be the only way he'd ever hear anyone call him "Senator.")
Anyway, the calling card for Phelps' Andy Ladd is that, at the play's (jarringly abrupt) end, when he writes his last letter after Williams' character has I think committed suicide, he bursts into tears. I guess it's all anyone ever talks about - the surprise of it, how sensitive Digger is and how he really has some talent at this acting thing. Whatever. The tortured whine of his bawling reminded me of the old acting saw that one shouldn't "act drunk" when playing a drunk.
As the audience of maybe 50 applauded, he wiped his face and blew his nose. Then Digger was back. He sat on his desk, unbuttoned his suit jacket and laid out a 10-minute chalk talk on his acting philosophy, his love of community theater and how taking theater and instrumental music out of the schools forces inner-city kids to turn to rap music and other criminal activities.
Admittedly, Phelps was preaching to the choir. Most of the folks there seemed to know each other. Whether they were well-scrubbed Fordham Irish or Irish Irish, I don't know, but even some former players showed up - three middle-aged white guys who could have only made a college squad (even Fordham's) in the 1970s and maybe '80s.
One black guy stood out in the audience. He was about 6'5", pretty well built. The right age to have played for Digger's Irish, maybe. Turns out he was a friend of the producer.
If not for him, the audience at the Helen Mills was a lot like the satisfied and clannish crowds at the Irish Repertory Theatre in Chicago - though the ladies didn't guffaw as loud as the men, and no one had pints to slosh all over their neighbors. Still, they were Tribe, and hooted obligingly when Digger delivered lines like, "I don't think you can be smart and Catholic at the same time."
For what it's worth, being among friends prob'ly allowed Phelps to do what little acting the play actually asked of him. His Andy was convincingly straight and proper - and properly mortified at one point to have to discuss a bout of teenaged impotence.
The way Phelps explained it, he gets a lot of acting practice working for ESPN - so he's pretty good at acting like he's listening when it's Dick Vitale's turn to talk. Now if only someone would tell him that playing the part of a college basketball analyst doesn't mean "acting like a college basketball analyst."
Related
Three Teams That Screwed Up 2026 NFL Draft
Red Sox Fire Alex Cora: What It Means for Boston’s Future
What the NBA Draft Should Learn From the 2026 NFL Draft
Best Betting Picks for Saturday’s NBA Playoff Matchups
Four Teams That Are Winning 2026 NFL Draft So Far
- MLB Best Bets Today: Strikeout Props and Total Plays to Target
- NBA Playoffs Betting Picks: Game 3 Predictions & Best Bets
- NBA Playoff Picks: Rockets vs Lakers & Spurs vs Blazers Best Bets
- MLB Betting Picks Today: Two Expert Picks for Tuesday’s Slate
- NBA Playoff Picks: Best Bets for Nuggets vs Timberwolves & Knicks vs Hawks
- Best Value Betting Picks Ahead of 2026 NFL Draft
- UFC Winnipeg Betting Picks: Best Bets for April 18th Card

