60 Days in Jail
10.25pm, Channel 4
Season two of the hardcore US reality show set in an Indiana prison rigged with 300 cameras. Eight volunteers go undercover as prisoners with only the local sheriff aware of their true identities. A former cop is among the first intake of this new series, as well as a mother hoping to gain some insight into her own daughter’s incarceration. Graeme Virtue
Dispatches: Secrets of Britain’s New Homes
8pm, Channel 4
The horror of Grenfell Tower has rendered visceral and tangible what has been blindingly obvious for years. Britain faces a housing crisis of monumental proportions and politicians seem paralysed by its magnitude. Beginning a week of related programming on Channel 4, this doc sees Antony Barnett tracking the links between the current government and the property industry. Phil Harrison
How to Retire at 40
8.30pm, Channel 4
“Supersaving”. Trend-spotting. Taking a risk. These are the three paths identified here as a way of achieving the goal stated in the title. Obviously, it’s the risk-takers who make it more fun. Take Pippa: she raised £120,000 in nine days on a crowdfunding site to market her range of nut butters – then turned over £3m last year. John Robinson
Catching a Killer: The Wind in the Willows Murder
9pm, Channel 4
If there is one thing more gripping than fictional police procedurals, it’s real police officers doing real police work. Tonight’s episode of this absorbing series chronicles the hunt for the killer of Adrian Greenwood, a book dealer stabbed to death in his Oxford home last year: an early edition of the titular classic was missing. Andrew Mueller
Storyville: This Was My Dad – the Rise and Fall of Geoffrey Matthews
10pm, BBC4
It’s a tough watch, this candid film from documentary-maker Morgan Matthews who, in an attempt to reconnect with his estranged dad, Geoff, chronicled the ailing health and finances of the former high flyer and his eccentric fortune-telling wife Anna for more than a decade – right up to the moment of Geoff’s death. But it’s also funny and warm. Ali Catterall
Katie Price: My Crazy Life
10pm, Quest Red
She has written books, made music and posed topless, but reality TV is arguably Pricey’s truest form of creative expression. This new series may surprise with its artistry: lingering closeups of third husband Kieran’s unguarded expressions and 11-year-old Junior providing the Iago-like asides. Here’s his verdict on the new single: “She just shouts.” Ellen E Jones
Convicted for Love
10pm, More4
Britain’s shameful history of denigrating, oppressing and deceiving gay citizens is explored in a documentary marking half a century since the Sexual Offences Act 1967. That was rightly hailed as a victory, but it only partly decriminalised homosexuality; this year’s “Turing law” promised atonement, but in practice a tiny minority of those convicted have been pardoned. The film tells the story of four men whose lives have been blighted by state discrimination. Jack Seale
Film choice
Nymphomaniac: Volume I (Lars von Trier, 2013) 11.35pm, Film4
When the lonely and vulnerable Seligman (Stellan Skarsgård) invites the battered Joe (Charlotte Gainsbourg) into his home, it’s the start of a curiously beautiful friendship. Over cups of tea, and two whole films, she recounts her life of sexual obsession – an odyssey featuring a cast of thousands, including cameos by Shia LaBeouf (awkward), Uma Thurman (angry) and Jamie Bell (all but unwatchable), while the chimerical Von Trier steers his sparkling course through the erotic and the absurd. Volume II shows on Tuesday.
Live sport
Test Cricket: England v South Africa 10.30am, Sky Sports 2. The final day from Lord’s.
Tennis: Wimbledon 2017 11.30am, BBC2. More from the All England Club, where the men’s and women’s fourth-round singles matches are due to get under way.
World League Hockey: England v Poland 3pm, BT Sport 1. Coverage of the Pool A match in the women’s hockey world league semi-finals.
